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Hexamethylphosphoramide structure
Hexamethylphosphoramide structure

Hexamethylphosphoramide

Iupac Name:N-[bis(dimethylamino)phosphoryl]-N-methylmethanamine
CAS No.: 680-31-9
Molecular Weight:179.20000
Modify Date.: 2022-11-10 23:04
Introduction: 1. It can be used as the efficient anti-corrosion agent of PVC and other kinds of chlorine-containing resin products and coatings.2. The product is the weathering solvent of polyvinyl chloride and excellent polar solvent, having a significant effect on the low temperature resistance and aging resistance of the agricultural film; it is a multi-functional high-boiling polar solvent that is aprotic. It can be used as the solvents of polymer synthesis with special effect on the synthesis of polyphenylene sulfide and aromatic polyamide and so on. This product, as the co-catalyst of propylene polymerization catalyst, when supplied to the ethylene propylene rubber, can improve the missile and oil resistance of the latter one. Hexamethylphosphoramide can also be used as a gas chromatographic fixative, ultraviolet inhibitor, rocket fuel additives for lowering the freezing point and chemical sterilizers.3. It is effective non-proton solvent; as fixative of gas chromatography (highest usage temperature: 35°C with methanol as the solvent); used for separation and analysis of hydrocarbons; for separation of alkanes, alkenes and alkynes; accelerator of stereo-specific reaction; Ultraviolet inhibitor of PVC. View more+
1. Names and Identifiers
1.1 Name
Hexamethylphosphoramide
1.2 Synonyms

Eastman Inhibitor HPT eastmaninhibitorhpt EINECS 211-653-8 ENT 50,882 ENT 50882 HEMPA HEXAMETAPOL hexamethyl hexamethylphosphoric acid triamide hexamethylphosphoric triamide hexamethyl-phosphoric triamide Hexmethylphosphoramide HMPA HMPTA HPT MFCD00008303 N,N,N',N',N'',N''-hexamethyl-phosphoric triamide Phosphoric acid hexamethyltriamide PO(NMe2)3 (hexamethylphosphorous triamide) tris(dimethylamino)phosphine oxide

1.3 CAS No.
680-31-9
1.4 CID
12679
1.5 EINECS(EC#)
211-653-8
1.6 Molecular Formula
C6H18N3OP (isomer)
1.7 Inchi
InChI=1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
1.8 InChkey
GNOIPBMMFNIUFM-UHFFFAOYSA-N
1.9 Canonical Smiles
CN(C)P(=O)(N(C)C)N(C)C
1.10 Isomers Smiles
CN(C)P(=O)(N(C)C)N(C)C
2. Properties
3.1 Density
1.03g/mLat 25°C(lit.)
3.1 Melting point
7°C(lit.)
3.1 Boiling point
230-232°C740mm Hg(lit.)
3.1 Refractive index
n20/D 1.459(lit.)
3.1 Flash Point
222°F
3.2 Precise Quality
179.11900
3.2 PSA
36.60000
3.2 logP
0.77930
3.2 VaporDensity
6.18 (vs air)
3.3 Appearance
clear colorless to light amber liquid
3.4 Storage
this compound should be handled only in a fume hood, using appropriate impermeable gloves and splash goggles to prevent skin and eye contact. Containers of this substance should be stored in secondary containers.
3.5 Carcinogenicity
Hexamethylphosphoramide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
3.6 Chemical Properties
It appears as colorless transparent flammable liquid with a medium ammonia flavor. It is soluble in water, polar and non-polar solvents.
3.7 Color/Form
COLORLESS, MOBILE LIQUID
Clear, colorless liquid [Note: A solid below 43 degrees F].
3.8 Flammability and Explosibility
Combustible liquid. Its decomposition at high temperatures or in a fire can produce phosphine, phosphorus oxides, and oxides of nitrogen, which are extremely toxic. Carbon dioxide or dry chemical extinguishers should be used for HMPA fires.
3.9 Odor
Spicy odor (no threshold data)
3.10 pKa
4.69±0.70(Predicted)
3.11 Water Solubility
Miscible
3.12 Spectral Properties
INDEX OF REFRACTION: 1.4572 @ 21 DEG C/D
Intense mass spectral peaks: 44 m/z (100%), 135 m/z (73%), 45 m/z (67%), 42 m/z (25%)
IR: 1551 (Documentation of Molecular Spectroscopy Collection)
MASS: 1217 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
3.13 Stability
Stable. Incompatible with strong acids, strong oxidizing agents.
3.14 StorageTemp
Inert atmosphere,Room Temperature
3. Use and Manufacturing
4.1 Potential Exposure
Hexamethylphosphoric triamide is amaterial possessing unique properties and is widely used asa solvent in small quantities, in organic and organometallicreactions in laboratories. This is the major source of occu pational exposure to HMPA in the United States. It is alsoused as a processing solvent in the manufacture of aramidfibers. HMPA has been evaluated for use as an ultravioletlight absorber or inhibitor in polyvinylchloride formulations;as an additive for antistatic effects; as a flame retardant; andas a deicing additive for jet fuels. Hexamethylphosphorictriamide has also been extensively investigated as an insectchemosterilant.
4.2 Purification Methods
The industrial synthesis is usually by treatment of POCl3 with excess of dimethylamine in isopropyl ether. Impurities are water, dimethylamine and its hydrochloride. It is purified by refluxing over BaO or CaO at about 4mm pressure in an atmosphere of nitrogen for several hours, then distilled from sodium at the same pressure. The middle fraction (b ca 90o) is collected, refluxed over sodium under reduced pressure under nitrogen and distilled. It is kept in the dark under nitrogen, and stored in solid CO2. It can also be stored over 4A molecular sieves. Alternatively, it is distilled under vacuum from CaH2 at 60o and is crystallised twice in a cold room at 0o, seeding the liquid with crystals obtained by cooling in liquid nitrogen. After about two-thirds are frozen, the remaining liquid is drained off [Fujinaga et al. Pure Appl Chem 44 117 1975]. For tests of purity see Fujinaga et al. in Purification of Solvents, Coetzee Ed., Pergamon Press, Oxford, 1982. For efficiency of desiccants in drying HMPA see Burfield and Smithers [J Org Chem 43 3966 1978, Sammes et al. J Chem Soc, Faraday Trans 1 281 1986]. [Beilstein 4 IV 284.] CARCINOGEN.
4.3 Shipping
UN3082 Environmentally hazardous substances,liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz ardous material, Technical Name Required
4.4 Usage
1. It can be used as the efficient anti-corrosion agent of PVC and other kinds of chlorine-containing resin products and coatings.2. The product is the weathering solvent of polyvinyl chloride and excellent polar solvent, having a significant effect on the low temperature resistance and aging resistance of the agricultural film; it is a multi-functional high-boiling polar solvent that is aprotic. It can be used as the solvents of polymer synthesis with special effect on the synthesis of polyphenylene sulfide and aromatic polyamide and so on. This product, as the co-catalyst of propylene polymerization catalyst, when supplied to the ethylene propylene rubber, can improve the missile and oil resistance of the latter one. Hexamethylphosphoramide can also be used as a gas chromatographic fixative, ultraviolet inhibitor, rocket fuel additives for lowering the freezing point and chemical sterilizers.3. It is effective non-proton solvent; as fixative of gas chromatography (highest usage temperature: 35°C with methanol as the solvent); used for separation and analysis of hydrocarbons; for separation of alkanes, alkenes and alkynes; accelerator of stereo-specific reaction; Ultraviolet inhibitor of PVC.
4.5 Waste Disposal
Excess hexamethylphosphoramide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines. Hexamethylphosphoramide Preparation Products And Raw materials Preparation Products
4. Safety and Handling
5.1 Symbol
GHS08;
5.1 Hazard Codes
T
5.1 Signal Word
DANGER
5.1 Risk Statements
R45; R46
5.1 Safety Statements
S53-S45
5.1 Packing Group
III
5.1 Fire Hazard
Combustible liquid. Its decomposition at high temperatures or in a fire can producephosphine, phosphorus oxides, and oxides of nitrogen, which are extremely toxic.Carbon dioxide or dry chemical extinguishers should be used for HMPA fires.
5.2 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/
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
5.3 Hazard Class
6.1(b)
5.3 Hazard Declaration
H340; H350
5.3 Cleanup Methods
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
5.4 DisposalMethods
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/
5.5 RIDADR
2810
5.5 Caution Statement
P201; P308 + P313
5.5 Incompatibilities
Incompatible (possibly violent reaction;fire and explosions) with oxidizers (chlorates, nitrates,peroxides, permanganates, perchlorates, chlorine, bromine,fluorine, etc.). Keep away from alkaline materials, chemi cally active metals, strong acids, strong bases.
5.6 WGK Germany
3
5.6 RTECS
TD0875000
5.6 Protective Equipment and Clothing
PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... 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. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Recommendations for respirator selection. Condition: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: Respirator Class(es): Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive-pressure mode.
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Class(es): Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister. Any appropriate escape-type, self-contained breathing apparatus.
5.7 Reactivities and Incompatibilities
Oxidizers, strong acids, chemically active metals (e.g., potassium, sodium, magnesium, zinc).
5.8 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 . 15 , 1977,p. 211.(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.

5.9 Safety

Hazard Codes: ToxicT
Risk Statements: 45-46 
R45:May cause cancer. 
R46:May cause heritable genetic damage.
Safety Statements: 53-45-9 
S53:Avoid exposure - obtain special instructions before use. 
S45:In 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.
RIDADR: 2810
WGK Germany: 3
RTECS: TD0875000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 680-31-9(Hazardous Substances Data)
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion, skin contact, intraperitoneal, and intravenous routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of phosphine, POx, and NOx.

5.10 Specification

 Hexamethylphosphoramide (CAS NO.680-31-9) is also named as AI3-50882 ; CCRIS 332 ; ENT 50882 ; Eastman ; Inhibitor HPT ; HSDB 2031 ; Hempa ; Hexametapol ; Hexamethyl phosphoramide ; Hexamethylfosforamid ; Hexamethylfosforamid [Czech] ; Hexamethylorthophosphoric triamide ; Hexamethylphosphoric acid triamide ; Hexamethylphosphoric triamide ; N,N,N,N,N,N-Hexamethylphosphoric triamide ; NSC 113131 ; NSC 7967 ; Phosphoric acid hexamethyltriamide ; Phosphoric hexamethyltriamide ; Phosphoric triamide, hexamethyl- ; Phosphoric tris(dimethylamide) ; Phosphoryl hexamethyltriamide ; Tris(dimethylamino)phosphine oxide ; Tris(dimethylamino)phosphorus oxide ; Tris-(dimethylamid) kyseliny fosforecne ; Tris-(dimethylamid) kyseliny fosforecne [Czech] . Hexamethylphosphoramide (CAS NO.680-31-9) is clear colorless to light amber liquid with a spicy odor. It is soluble in water. Hexamethylphosphoramide may react with strong oxidizing agents and strong acids. It is susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Hexamethylphosphoramide is combustible. 

5.11 Toxicity
1.    

dns-hmn:hla 125 mg/L

    PMRSDJ    Progress in Mutation Research. 5 (1985),375.
2.    

cyt-hmn:lym 500 mg/L

    MUREAV    Mutation Research. 156 (1985),19.
3.    

sce-rat:lvr 2 g/L

    PMRSDJ    Progress in Mutation Research. 5 (1985),287.
4.    

ihl-rat TCLo:50 ppb/52W-C:CAR

    AJPAA4    American Journal of Pathology. 106 (1982),8.
5.    

orl-rat LD50:2650 mg/kg

    NATUAS    Nature. 211 (1966),146.
6.    

skn-rat LDLo:3500 mg/kg

    NATUAS    Nature. 211 (1966),146.
7.    

orl-mus LD50:2400 mg/kg

    NYKZAU    Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. 70 (1974),114P.
8.    

ipr-mus LD50:1600 mg/kg

    PMRSDJ    Progress in Mutation Research. 1 (1981),682.
9.    

ivn-mus LD50:800 mg/kg

    CHINAG    Chemistry and Industry.(36),(1966),1529.
10.    

orl-rbt LDLo:1500 mg/kg

    JEENAI    Journal of Economic Entomology. 48 (1955),139.
11.    

skn-rbt LD50:2600 mg/kg

   
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 1B

Carcinogenicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H340 May cause genetic defects

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

9. Other Information
9.0 General description
Hexamethylphosphoramide is made from the reaction of dimethylamine and phosphorus oxychloride. It has a molecular weight of 179.2, appearing as colorless or light yellow transparent liquid with slightly astringent taste. It has a relative density of 1.0253~1.0257 (20 ℃), refractive index of 1.4582~1.4589 (20 °C), the freezing point of 2~7 °C and the boiling point of 116~117 °C (1480Pa). It is soluble in polar and non-polar solvents. It is also miscible with the commonly used plasticizers such as dioctyl phthalate, dioctyl sebacate, and triphenyl phosphite in any proportion. It has a similar toxicity to phosphate. Avoid contact with skin. Its containers should be tightly sealed to prevent leakage and water absorption to be deteriorated Hexamethylphosphoramide is the light stabilizer of the PVC, enabling an excellent anti-aging properties of outdoor products with excellent weather resistance, therefore being known as highly-efficient weathering agent of PVC.
Addition of 2 to copies of this product to the PVC film can significantly improve both the weather resistance and cold resistance as well as reducing the processing temperature by 10 °C. This product can also be used as the excellent polar solvent of many kinds of polymer materials such as polyphenylene sulfide, polyurethane and polyamide for improving the resin quality, simplifying the process and reducing costs. Addition it into the ethylene-propylene rubber can improve the flexibility and oil resistance. It can also be used as a co-catalyst for the polymerization of propylene to improve the catalytic efficiency of the main catalyst.
9.1 Harmful effects and symptoms of poisoning
To animals: Hexamethylphosphoramide (HMPA) is known to have various kinds of toxic effects on experimental animals. HMPA-induced acute poisoning in rats is characterized with nephropathy, severe bronchiectasis and bronchial pneumonia. Application of HMPA repetitively to rabbit skin can lead to weight loss, changes in gastric function and apparent neurological disorders. Rats subjecting to oral administration of HMPA can exhibit testicular atrophy and semen deficiencies. Small chickens subjecting to oral administration of HMPA can also get highly inhibited growth in its testis. HMPA has been known to induce mutagenesis in Drosophila. However, the effects of HMPA on sex chromosomes in mice showed that the frequency of chromosome aberration induced by HMPA was not significant compared with the control group. Preliminary results of the toxicity study upon inhaling HMPA revealed that nasal tumors will appear in rats after 8 months after being exposed to 400 to 4000 ppb HMPA. In some diseased mice, cancer initiated from the epithelium connecting the nasal bone can fill the nasal cavity and penetrates into the brain. Rats exposed to 50 ppb HMPA didn’t develop nasal cancer compared with the control group.
To humans: the role of HMPA on human toxicity has not been reported.
9.2 Protective measures
The traditional measure is that the operator should wear protective clothing, wearing protective glasses and gloves, to avoid direct contact with the product with the production site should be well ventilated.
9.3 Chemical properties
It appears as colorless transparent flammable liquid with a medium ammonia flavor. It is soluble in water, polar and non-polar solvents.
9.4 Uses
1.   It can be used as the efficient anti-corrosion agent of PVC and other kinds of chlorine-containing resin products and coatings.
2.   The product is the weathering solvent of polyvinyl chloride and excellent polar solvent, having a significant effect on the low temperature resistance and aging resistance of the agricultural film; it is a multi-functional high-boiling polar solvent that is aprotic. It can be used as the solvents of polymer synthesis with special effect on the synthesis of polyphenylene sulfide and aromatic polyamide and so on. This product, as the co-catalyst of propylene polymerization catalyst, when supplied to the ethylene propylene rubber, can improve the missile and oil resistance of the latter one. Hexamethylphosphoramide can also be used as a gas chromatographic fixative, ultraviolet inhibitor, rocket fuel additives for lowering the freezing point and chemical sterilizers.
3.   It is effective non-proton solvent; as fixative of gas chromatography (highest usage temperature: 35°C with methanol as the solvent); used for separation and analysis of hydrocarbons; for separation of alkanes, alkenes and alkynes; accelerator of stereo-specific reaction; Ultraviolet inhibitor of PVC.
9.5 Production method
It can be obtained through the reaction between dimethylamine and alkali chlorophosphorus. Put the dimethylamine and phosphorus oxychloride for reaction in triethylene glycol as the solvent; control the temperature at 40-60 °C; upon reaction, add ammonia as acid-binding agent with interaction with the generated hydrogen chloride to become ammonium chloride precipitation. After completion of the reaction, filtration was performed. Recycle the trichlorethylene from the filtration and then perform alkali treatment, and then conduct distillation, collecting the fraction of 113-118 °C (2.0kPa) fractions to derive Hexamethylphosphoramide (HMPA). Tsinghua Unisplendour Group Corporation has cooperated with the production plant to develop a new solvent-free process that can achieve a product purity of 99.2% or more. The industrial hexamethylphosphoramide appears as colorless or light yellow transparent liquid. Catalyst grade content ≥ 99.5%; first-class grade ≥ 99.0%; second-class products ≥ 98.0%. Fixed consumption amount of raw materials: dimethylamine 2410kg/t, phosphorus oxychloride: 1610kg/t, liquid ammonia 430kg/t.
9.6 Chemical Properties
colourless or light amber liquid with an aromatic spicy odour
9.7 Chemical Properties
Hexamethylphosphoric triamide is a colorless liquid with a spicy odor.
9.8 Uses
Aprotic solvent in organic synthesis. Solvent for polymers, gases; polymerization catalyst; thermal stabilizer in polystyrene; protective additive for polyvinyl and polyolefin resins against uv light degradation. De-icing additive for jet fuels. Chemosterilant for a number of insect pests; chemical mutagen.
9.9 Uses
Solvent for polymers; polymerization catalyst; stabilizer against thermal degradation in polystyrene; UV stabilizer in polyvinyl and polyolefin resins
9.10 Uses
Hexamethylphosphoramide is a dipolar co-solvent and an effective additive used in reactions like reduction of halides, deoxygenation of sulfones, halide olefin couplings and cleavage of carbon-sulfur bond.
9.11 Merck
14,4725
9.12 BRN
1099903
10. Computational chemical data
  • Molecular Weight: 179.20000g/mol
  • Molecular Formula: C6H18N3OP
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 179.11874920
  • Monoisotopic Mass: 179.11874920
  • Complexity: 139
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 26.8
  • Heavy Atom Count: 11
  • 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: AAADceBjIAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAFAAAgCAAAAAAAAQCAAIAAAAAQAAAAAAAAAAAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
  • Description Hexamethylphosphoramide is made from the reaction of dimethylamine and phosphorus oxychloride. It has a molecular weight of 179.2, appearing as colorless or light yellow transparent liquid with slightly astringent taste. It has a relative density of 1.0253~1.0257 (20 ℃), refractive ind...
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