Urethane

Iupac Name：ethyl carbamate

CAS No.: 51-79-6

Molecular Weight：89.09

Modify Date.: 2022-10-31 06:27

Introduction: Ethyl carbamate occurs as colourless or white columnar crystals or granular powder. It isvery soluble in water. With heat, ethyl carbamate undergoes decomposition and emits toxicfumes of carbon monoxide, carbon dioxide, and nitrogen oxides. Ethyl carbamate is usedas an intermediate in the synthesis of a number of chemical products, for example, pharmaceuticals,in biochemical research and medicine, and as a solubiliser and co-solvent forpesticides and fumigants.Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment ofmultiple myeloma before it was found to be toxic, carcinogenic, and largely ineffective.However, due to U.S. FDA regulations, ethyl carbamate has been withdrawn from pharmaceuticaluse. However, small quantities of ethyl carbamate are also used in laboratoriesas an anaesthetic for animals. View more+

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1. Names and Identifiers

1.1 Name: Urethane
1.2 Synonyms: 2-Ethyl Hexanoate A 11032 a11032 Aethylcarbamat Aethylurethan ai3-00553 Aminoformicacidethylester. caproic acid ethyl ester Capronic ether absolute Carbamate, Ethyl carbamated’ethyle Carbamic Acid Ethyl Ester Carbamic acid, ethyl ester Carbamic acid, ethyl ester (8CI 9CI) EINECS 200-123-1 Ethyl caproate ethyl capronate Ethyl Carbamate ethyl carbaminate ethyl ester of carbamic acid Ethyl hexoate ethyl n-heptanoate Ethyl urethan Ethyl urethane Hexanoic acid,ethyl ester methyl,methyl carbamate MFCD00007966

1.3 CAS No.: 51-79-6

1.4 CID: 5641

1.5 EINECS(EC#): 200-123-1

1.6 Molecular Formula: C3H7NO2 (isomer)

1.7 Inchi: InChI=1S/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)

1.8 InChkey: JOYRKODLDBILNP-UHFFFAOYSA-N

1.9 Canonical Smiles: CCOC(=O)N

1.10 Isomers Smiles: CCOC(=O)N

2. Properties

2.1 Density: 1.10

2.1 Melting point: 48-50 °C(lit.)

2.1 Boiling point: 182-184 °C(lit.)

2.1 Refractive index: 1.4144

2.1 Flash Point: 198 °F

2.2 Precise Quality: 89.04770

2.2 PSA: 52.32000

2.2 logP: 0.80190

2.2 Solubility: slightly soluble

2.3 VaporDensity: 3.07 (vs air)

2.4 Appearance: white crystalline powder

2.5 Storage: Ambient temperatures.

2.6 Carcinogenicity: Urethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

2.7 Chemical Properties: Colorless crystals or white powder;odorless, saltpeter-like taste. Solutions neutral to litmus. Soluble in water,alcohol, ether, glycerol, and chloroform; slightlysoluble in olive oil. Combustible.

2.8 Color/Form: White

2.9 PH: pH(50g/l, 25℃) : 5.0～7.0

2.10 pKa: 13.58±0.50(Predicted)

2.11 Water Solubility: slightly soluble

2.12 Spectral Properties: Index of refraction: 1.4144 at 51 deg C/D
IR: 5961 (Coblentz Society Spectral Collection)
NMR: 245 (Sadtler Research Laboratories Spectral Collection)
C13NMR: 37 (Johnson and Jankowski carbon 13 NMR Spectra. John Wiley and Sons, New York.)
MASS: 707 (NIST/EPA/MSDC Mass Spectral Database. 1990 version)

2.13 Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.

2.14 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Definition: A poisonous flammableorganic compound, used in medicine, as asolvent, and as an intermediate in the manufacture of polyurethane resins.

3.2 Potential Exposure: Urethane is used as a chemical intermediatein manufacture of pharmaceuticals; pesticides, andfungicides; in the preparation of amino resins. It may bereacted with formaldehyde to give cross-linking agentswhich impart wash-and-wear properties to fabrics. It hasalso been used as a solubilizer and cosolvent in the manufactureof pesticides, fumigants, and cosmetics. It was formerlyused in the treatment of leukemia. It occurs whendiethylpyrocarbonate, a preservative used in wines, fruitjuices, and soft drinks, is added to aqueous solutions.

3.3 Purification Methods: Urethane is best purified by fractional distillation, but it can be 20 25 1.4144. sublimed at ~103o/~50mm. It has also been recrystallised from *benzene. Its solubilitiy at room temperature is 2g/mL in H2O, 1.25g/mL in EtOH, 1.1g/mL in CHCl3, 0.67g/mL in Et2O and 0.03g/mL in olive oil. It is a suspected human carcinogen.[Beilstein 3 H 22, 3 IV 40.]

3.4 Usage: The primary use of urethane has been as a chemical intermediate in preparation of amino resins (IARC 1974). The process involves a reaction with formaldehyde to give hydroxymethyl derivatives that are used as cross-linking agents in permanent-press textile treatments designed to impart wash-and-wear properties to fabrics. Urethane isalso used as a solubilizer and co-solvent in the manufacture of pesticides, fumigants, and cosmetics, as an intermediate in the manufacture of pharmaceuticals, and in biochemical research (HSDB 2009). Urethane was formerly used as an active ingredient in drugs prescribed for the treatment of neoplastic diseases, as a sclerosing solution for varicose veins, as a hypnotic, and as a topical bactericide. It is also used in veterinary medicine as an anesthetic (IARC 1974). Urethane is produced naturally during many fermentation processes(Zimmerli and Schlatter 1991).

4. Safety and Handling

4.1 Symbol: GHS07, GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: 45-22

4.1 Safety Statements: 53-45-99

4.1 Octanol/Water Partition Coefficient: log Kow = -0.15

4.2 Other Preventative Measures: PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

4.3 Hazard Declaration: H302-H350

4.3 DisposalMethods: Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U238, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... Summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
The following wastewater treatment technologies have been investigated for urethane: Biological treatment.
These compounds are all hydrolyzed using 5 M sodium hydroxide solution, although the reaction times vary. Methyl carbamate is hydrolyzed to methanol and carbamic acid and urethane /ethyl carbamate/ is hydrolyzed to ethanol and carbamic acid. ... Carbamic acid decomposes to carbon dioxide and ammonia ... In all cases destruction is greater than 99% and good accountances are obtained for the products ... .

4.4 RIDADR: UN 3077 9 / PGIII

4.4 FirePotential: Combustible

4.5 Safety Profile: Confirmed carcinogenwith experimental carcinogenic,neoplastigenic, and tumorigenic data. Atransplacental carcinogen. Moderately toxicby ingestion, intraperitoneal, subcutaneous,intramuscular, parenteral, and intravenousroutes. An experimental teratogen.Experimental reproductive effects. Humanmutation data reported. Causes depressionof bone marrow and occasionally focaldegeneration in the brain. Can also producecentral nervous system depression, nauseaand vomiting. Has been found in over 1000beverages sold in the United States. Themost heavily contaminated liquors arebourbons, sherries, and fruit brandies (some had 1000 to 12,000 ppb urethane). Manywhiskeys, table and dessert wines, brandies,and liqueurs contain potentially hazardousamounts of urethane. The allowable limit forurethane in alcoholic beverages is 125 ppb.It is formed as a side product duringprocessing.Hot aqueous acids or alkalies decomposeurethane to ethanol, carbon dioxide, andammonia. Reacts with phosphoruspentachloride to form an explosive product.When heated it emits toxic fumes of NOx.Used as an intermedate in the manufactureof pharmaceuticals, pesticides, andfungicides. See also CARBAMATES.

4.6 Caution Statement: P201-P301 + P312 + P330-P308 + P313

4.6 Formulations/Preparations: GRADES: Technical; NF.

4.7 Incompatibilities: Dust may form explosive mixture withair. Incompatible with oxidizers (chlorates, nitrates, peroxides,permanganates, perchlorates, chlorine, bromine, fluorine,etc.); contact may cause fires or explosions. Keepaway from alkaline materials, strong bases, strong acids,oxoacids, epoxides, gallium, perchlorate.

4.8 WGK Germany: 3

4.8 RTECS: FA8400000

4.8 Reactivities and Incompatibilities: This intermediate /N-carbomethoxymethylimino phosphoryl chloride/ (or its ethyl homologue), produced during prepn of phosphoryl dichloride isocyanate from interaction of phosphorus pentachloride & methyl (or ethyl) carbamate, is unstable. Its decomposition to the required product may be violent or explosive unless moderated by the presence of a halogenated solvent.
Incompatibilities: alkalies, acids, antipyrine, chloral hydrate, camphor, menthol, salol, or thymol.
Hot aqueous acids or alkalies decompose urethane to ethanol, carbon dioxide, and ammonia.
Reacts with phosphorous pentachloride to form and explosive product.

4.9 Report: NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 111.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.10 Safety

Hazard Codes of Urethane (CAS NO.51-79-6): T
Risk Statements: 45
R45: May cause cancer.
Safety Statements: 53-45-9
S53: Avoid exposure - obtain special instructions before use.
S45:I n case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S9: Keep container in a well-ventilated place.
WGK Germany: 3
RTECS: FA8400000
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. A transplacental carcinogen. Moderately toxic by ingestion, intraperitoneal, subcutaneous, intramuscular, parenteral, and intravenous routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. Causes depression of bone marrow and occasionally focal degeneration in the brain. Can also produce central nervous system depression, nausea and vomiting. Has been found in over 1000 beverages sold in the United States. The most heavily contaminated liquors are bourbons, sherries, and fruit brandies (some had 1000 to 12,000 ppb urethane). Many whiskeys, table and dessert wines, brandies, and liqueurs contain potentially hazardous amounts of urethane. The allowable limit for urethane in alcoholic beverages is 125 ppb. It is formed as a side product during processing.

Hot aqueous acids or alkalies decompose urethane to ethanol, carbon dioxide, and ammonia. Reacts with phosphorus pentachloride to form an explosive product. When heated it emits toxic fumes of NO_x. Used as an intermediate in the manufacture of pharmaceuticals, pesticides, and fungicides. See also CARBAMATES.

View all

4.11 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LDLo	oral	2188mg/kg (2188mg/kg)		"Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
guinea pig	LDLo	intraarterial	800mg/kg (800mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
guinea pig	LDLo	intravenous	800mg/kg (800mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
mouse	LD50	intraperitoneal	1539mg/kg (1539mg/kg)		Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
mouse	LD50	intravenous	500mg/kg (500mg/kg)		Acta Pharmaceutica Jugoslavica. Vol. 5, Pg. 43, 1955.
mouse	LD50	oral	2500mg/kg (2500mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 595, 1959.
mouse	LD50	subcutaneous	1750mg/kg (1750mg/kg)		Gann. Japanese Journal of Cancer Research. Vol. 63, Pg. 731, 1972.
mouse	LD50	unreported	2gm/kg (2000mg/kg)		British Journal of Cancer. Vol. 6, Pg. 160, 1952.
mouse	LDLo	parenteral	1gm/kg (1000mg/kg)	GASTROINTESTINAL: PERITONITIS	Progress Report for Contract No. PH-43-63-1132, Submitted to the National Cancer Institute by Scientific Associates, Inc. Vol. PH-43-62-483,
pigeon	LDLo	oral	800mg/kg (800mg/kg)		"Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit	LDLo	intravenous	2gm/kg (2000mg/kg)		"Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 272, 1973.
rat	LD50	intramuscular	1400mg/kg (1400mg/kg)		Zeitschrift fuer Krebsforschung und Klinische Onkologie. Vol. 84, Pg. 227, 1975.
rat	LD50	intraperitoneal	1500mg/kg (1500mg/kg)		Cancer Research. Vol. 26, Pg. 1448, 1966.
rat	LD50	oral	1809mg/kg (1809mg/kg)		Cancer Letters Vol. 57, Pg. 37, 1991.
rat	LDLo	subcutaneous	1800mg/kg (1800mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H350 May cause cancer
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : CCl4 solution

IR : KBr disc

IR : nujol mull

SOLUTION (CCl4 FOR 2-9.6, CS2 FOR 8.6-16 MICRON) VS SOLVENT

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

51-79-6Total: 37 Synthesis Route

625-57-0 4 Suppliers

4115-25-7

75-00-3 58 Suppliers

51-79-6 192 Suppliers

Literatures:
Chen, Lin; Thompson, Tracy R.; Hammer, Robert P.; Barany, George Journal of Organic Chemistry, 1996 , vol. 61, # 19 p. 6639 - 6645
Yield: ~52%

625-57-0 4 Suppliers

4115-25-7

75-00-3 58 Suppliers

51-79-6 192 Suppliers

178318-21-3

Literatures:
Journal of Organic Chemistry, , vol. 61, # 19 p. 6639 - 6645
Yield: ~16%

6971-74-0

644-08-6 83 Suppliers

20743-57-1

55-21-0 123 Suppliers

106-49-0 131 Suppliers

51-79-6 192 Suppliers

Literatures:
Angewandte Chemie, , vol. 92, # 8 p. 647 - 649
Yield: ~20%

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8. Other Information

8.0 Merck: 14,9874

8.1 BRN: 635810

8.2 Description: Ethyl carbamate occurs as colourless or white columnar crystals or granular powder. It is very soluble in water. With heat, ethyl carbamate undergoes decomposition and emits toxic fumes of carbon monoxide, carbon dioxide, and nitrogen oxides. Ethyl carbamate is used as an intermediate in the synthesis of a number of chemical products, for example, pharmaceuticals, in biochemical research and medicine, and as a solubiliser and co-solvent for pesticides and fumigants. Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment of multiple myeloma before it was found to be toxic, carcinogenic, and largely ineffective. However, due to U.S. FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anaesthetic for animals.

8.3 Chemical Properties: Colorless crystals or white powder; odorless, saltpeter-like taste. Solutions neutral to litmus. Soluble in water, alcohol, ether, glycerol, and chloroform; slightly soluble in olive oil. Combustible.

8.4 Chemical Properties: Urethane is a colorless, almost odorless crystalline solid or powder.

8.5 Occurrence: Urethane (ethyl carbamate) occurs as a natural byproduct in fermented products such as wine, liquors, yogurt, beer, bread, olives, cheeses, and soy sauces. Whereas urethane has a known cancer etiology in experimental animals, no such relationship has yet been proven in humans. Alcohol may act by blocking the metabolism of urethane, and thus exert a protective effect in humans consuming alcoholic beverages.

8.6 Uses: The primary use of urethane has been as a chemical intermediate in preparation of amino resins (IARC 1974). The process involves a reaction with formaldehyde to give hydroxymethyl derivatives that are used as cross-linking agents in permanent-press textile treatments designed to impart wash-and-wear properties to fabrics. Urethane isalso used as a solubilizer and co-solvent in the manufacture of pesticides, fumigants, and cosmetics, as an intermediate in the manufacture of pharmaceuticals, and in biochemical research (HSDB 2009). Urethane was formerly used as an active ingredient in drugs prescribed for the treatment of neoplastic diseases, as a sclerosing solution for varicose veins, as a hypnotic, and as a topical bactericide. It is also used in veterinary medicine as an anesthetic (IARC 1974). Urethane is produced naturally during many fermentation processes(Zimmerli and Schlatter 1991).

8.7 Uses: Naturally occurring contaminant in fermented foods, particularly wine, stone-fruit brandies, and bread. This substance is reasonably anticipated to be a human carcinogen.

8.8 Uses: antiinfective

8.9 Uses: Intermediate in organic synthesis. In the preparation and modification of amino resins. As solvent, solubilizer and cosolvent for various organic materials. Animal anesthetic in laboratory procedures.

8.10 Definition: A poisonous flammable organic compound, used in medicine, as a solvent, and as an intermediate in the manufacture of polyurethane resins.

8.11 World Health Organization (WHO): Urethane was formerly used as an antineoplastic agent in the treatment of chronic myeloid leukaemia. It is also a mild hypnotic which has been used as an anaesthetic for veterinary practice. It has been reported to have both a carcinogenic and mutagenic potential. Although urethane continues to be used as an industrial solvent, WHO has no information to suggest that it remains commercially available in pharmaceutical preparations.

8.12 General Description: Odorless colorless crystals or white powder. Sublimes readily at 217°F and 54 mm Hg. Cooling saline taste.

8.13 Air & Water Reactions: Water soluble. Aqueous solutions are neutral to litmus .

8.14 Reactivity Profile: Urethane is incompatible with alkalis, acids, chloral hydrate, camphor, menthol and thymol. Also incompatible with antipyrine and salol. May react with strong oxidizing agents. Liquefies with benzoic acid, resorcinol and salicylic acid. Reacts with phosphorus pentachloride to form an explosive product .

8.15 Hazard: Toxic by ingestion.

8.16 Safety Profile: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. A transplacental carcinogen. Moderately toxic by ingestion, intraperitoneal, subcutaneous, intramuscular, parenteral, and intravenous routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. Causes depression of bone marrow and occasionally focal degeneration in the brain. Can also produce central nervous system depression, nausea and vomiting. Has been found in over 1000 beverages sold in the United States. The most heavily contaminated liquors are bourbons, sherries, and fruit brandies (some had 1000 to 12,000 ppb urethane). Many whiskeys, table and dessert wines, brandies, and liqueurs contain potentially hazardous amounts of urethane. The allowable limit for urethane in alcoholic beverages is 125 ppb. It is formed as a side product during processing.Hot aqueous acids or alkalies decompose urethane to ethanol, carbon dioxide, and ammonia. Reacts with phosphorus pentachloride to form an explosive product. When heated it emits toxic fumes of NOx. Used as an intermedate in the manufacture of pharmaceuticals, pesticides, and fungicides. See also CARBAMATES.

8.17 Potential Exposure: Urethane is used as a chemical intermediate in manufacture of pharmaceuticals; pesticides, and fungicides; in the preparation of amino resins. It may be reacted with formaldehyde to give cross-linking agents which impart wash-and-wear properties to fabrics. It has also been used as a solubilizer and cosolvent in the manufacture of pesticides, fumigants, and cosmetics. It was formerly used in the treatment of leukemia. It occurs when diethylpyrocarbonate, a preservative used in wines, fruit juices, and soft drinks, is added to aqueous solutions.

8.18 Carcinogenicity: Urethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

8.19 Environmental Fate: Urethane may be released to the environment in various waste streams. If released to the atmosphere, urethane is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase urethane is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 2.2 days. If released to soil, urethane has very high mobility. Volatilization from moist soil surfaces does not occur. Biodegradation of urethane in soil may be important. If released into water, urethane is not adsorbed to suspended solids and sediment in the water column. Volatilization from water surfaces does not occur. The potential for bioconcentration in aquatic organisms is low based on an estimated bioconcentration factor (BCF) of 0.45. Urethane is resistant to hydrolysis under environmental conditions; hydrolysis half-lives of 3300 and 330 years at pH 7 and 8, respectively, were estimated for urethane. Urethane was judged easy to biodegrade in river die-away tests. Other biodegradation studies using activated sludge indicate urethane may biodegrade slowly.

8.20 Purification Methods: Urethane is best purified by fractional distillation, but it can be 20 25 1.4144. sublimed at ~103o/~50mm. It has also been recrystallised from *benzene. Its solubilitiy at room temperature is 2g/mL in H2O, 1.25g/mL in EtOH, 1.1g/mL in CHCl3, 0.67g/mL in Et2O and 0.03g/mL in olive oil. It is a suspected human carcinogen.[Beilstein 3 H 22, 3 IV 40.]

8.21 Toxicity evaluation: Urethane is activated in the liver into a carcinogenic metabolite. The activation of urethane by cytochrome P450 involves two sequential reactions. First, urethane is dehydrogenated to vinyl carbamate followed by epoxidation to form vinyl carbamate epoxide. The former is believed to be the ultimate carcinogenic metabolite of urethane.

8.22 Incompatibilities: Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, gallium, perchlorate.

8.23 Waste Disposal: Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration (incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions).

8.24 Usage: Ethyl carbamate in its molten state is good solvent for various organic materials, preparation & modification of amino resins, as solubilizer.

9. Computational chemical data

Molecular Weight: 89.09g/mol
Molecular Formula: C₃H₇NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 89.047678466
Monoisotopic Mass: 89.047678466
Complexity: 52.8
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 52.3
Heavy Atom Count: 6
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBCMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQAAAAAACggAICCABABAAIAAAAGAAAAAAAAAAAAAAAAAEAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What is the difference between an epoxy primer and a urethane primer? Jan 05 2022
First to apply in metal,epoxy primer,anti rust,second urethane primer,first coat,and finishing urehthane paint final coat
What solvents can solve aromatic urethane resins? Oct 28 2021
Do you have any information about chemical resistance of hexa-functional aromatic urethane acrylate? I want to know what solvents can solve aromatic urethane resins.
Flexible urethane additives in epoxies Oct 23 2021
For those who understand plastics and epoxies in particular, curious to know if I can add a correctly proportional amount of flexane urethane to epoxy paint without worrying about compatibility issues. IOW is there any non-typical or particular ingredient in epoxy that might prevent successful mixi...
Suitable safe cleaning solution for aliphatic urethane Oct 14 2021
I am looking for a suitable cleaning solution for a sprayed on coating that is an acrylic aliphatic urethane. My end goal would ideally be something that can neutralize rust, whiten and brighten the surface, and also include a powerful enough solvent that can loosen stuck on dirt/soap scum but not ...