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N,N-Dimethylformamide(CAS No. 68-12-2)

N,N-Dimethylformamide C3H7NO (cas 68-12-2) Molecular Structure

68-12-2 Structure

Identification and Related Records

【CAS Registry number】
Virodene-P 058
【Molecular Formula】
C3H7NO (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

Clear colorless liquid
【Melting Point】
【Boiling Point】
【Refractive Index】
【Flash Point】
0.94 o
Colorless to very slightly yellow liquid
Water-white liquid
【Storage temp】
Store at RT.
【Spectral properties】
MAX ABSORPTION (GAS): 162 NM (LOG E= 3.84); 197.4 NM (LOG E= 3.94)
Index of refraction: 1.42083 @ 25 deg C/D
IR: 156 (Sadtler Research Laboratories Prism Collection)
NMR: 39 (Varian Associates NMR Spectra Catalogue)
MASS: NIST 62666 (NIST/EPA/MCDC Mass Spectral Database 1990 version)
NMR: JJ 34 (Johnson and Janlowski, Carbon-13 NMR Spectra, John Wiley and Sons, NY, NY)
【Computed Properties】
Molecular Weight:73.09378 [g/mol]
Molecular Formula:C3H7NO
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:0
Exact Mass:73.052764
MonoIsotopic Mass:73.052764
Topological Polar Surface Area:20.3
Heavy Atom Count:5
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】
【Hazard Note】



Hazard Codes:?T
Risk Statements: 61-20/21-36?
R61:May cause harm to the unborn child.?
R20/21:Harmful by inhalation and in contact with skin.?
R36:Irritating to eyes.
Safety Statements: 53-45
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.)
RIDADR: UN 2265 3/PG 3
WGK Germany: 1
RTECS: LQ2100000
F: 3-10
Hazard Note: Toxic
HazardClass: 3
PackingGroup: III

【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
Strong irritant to skin ... .
Some complaints of eye irritation have resulted from vapor exposure in industry.
DMF was reported to be irritating to the eyes, mucous membranes, & the skin.
UN 2265
【Fire Potential】
Flammable liquid when exposed to heat or flame.
【DOT Emergency Guidelines】
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire: Caution: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane or nitroethane. Large fires: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces.
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
【Exposure Standards and Regulations】
Dimethylformamide is an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
Incompatible with carbon tetrachloride; alkyl aluminums.
Hot solutions of sodium tetrahydroborate (15.7% wt) in DMF will undergo a violent runaway thermal decomposition, the solid residue attaining a temperature of 310 deg C. The induction period depends on temperature and is 45 hr at 62 deg C and 45 min at 90 deg C.
... DMF /reacts violently when/ ... exposed to nitrates, chromic acid ...
Dimethylformamide contact with diisocyanatomethane causes violent polymerization of the isocyanate.
Cyanuric chloride reacts vigorously and exothermically with DMF after a deceptively long induction period. The 1:1 adduct initially formed decomposes above 60 deg C with evolution of carbon dioxide and formation of a dimeric unsaturated quaternary ammonium salt.
To effect reduction to the parent heterocycle, a solution of 2,5-bis-endo-dichloro-7-thiabicyclo(2.2.1)heptane in DMF was being added to a hot solution of sodium tetrahydroborate in the same solvent, when a violent explosion occurred. This may have arisen either from interaction of the dichloro cmpd with the solvent or from the known instability of hot solutions of the tetrahydroborate in DMF.
A mixture of triethylaluminium and DMF explodes when heated.
A mixture of sodium hydride and dimethylformamide was heated to, and held at 50 deg C. An exothermic reaction, which increased the temperature to 75 deg C, could not be controlled by external cooling and the pilot-scale reactor contents erupted. It was later found that an exotherm began to develop at 26 deg C ... and the subsequent reaction accelerated rapidly. Avoidance of holding mixtures hot is recommended, particularly when scaling up reactions.
Lithium azide and DMF are stable at 25 deg C during preparation of tert-alkyl azides, above 200 deg C the mixtures are shock-sensitive and highly explosive.
A vigorous reaction occurs on heating DMF with sodium metal.
There is a potentially dangerous reaction of carbon tetrachloride with dimethylformamide in presence of iron. The same occurs with 1,2,3,4,5,6-hexachlorocyclohexane.
Bromine and dimethylformamide interaction is extremely exothermic and under confinement in an autoclave the internal temperature and pressure exceeded 100 deg C and 135 bar, causing failure of the bursting disc.
After a thermal runaway reaction during chlorination in DMF solution, investigation revealed that saturated solutions of chlorine in DMF are hazardous, and will self-heat and erupt under either adiabatic or non-adiabatic conditions.
During oxidation of a sec-alcohol to ketone in cold DMF solution, addition of solid chromium trioxide caused ignition. Addition of lumps of trioxide was later found to cause local ignition on addition to ice-cooled DMF under nitrogen. Addition of 2 g chromium trioxide to 18 ml of solvent to form a 10% wt solution caused immediate ignition and ejection of the flask contents.
Addition of potassium permanganate to DMF to give a 20% (approx saturated) solution led to an explosion after 5 min. Subsequent tests on 1 g of oxidant with 5 g of solvent showed a rapid exotherm after 3-4 min, accompanied by popping noises from undissolved oxidant.
Magnesium nitrate has been reported to undergo spontaneous decomposition in DMF (possibly as a result of hydrolysis of the hexahydrate above its melting point of 90 deg C to liberate nitric acid).
Carbon tetrachloride; other halogenated compounds when in contact with iron; strong oxidizers; alkyl aluminums; inorganic nitrates.
Explosive reaction with bromine, potassium permanganate; triethylaluminum + heat. Forms explosive mixtures with lithium azide (shock sensitive above 200 deg C); uranium perchlorate.
Explosive reaction with bromine, potassium permanganate; triethylaluminum + heat. Forms explosive mixtures with lithium azide (shock sensitive above 200 deg C); uranium perchlorate.
Contact with carbon tetrachloride & other halogenated hydrocarbons, particularly when in contact with iron, as well as contact with strong oxidizing agents (e.g., methylene diisocyanate, halogens, & permanganates) may cause fires & explosions.
Ignition on contact with chromium trioxide.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
Workers exposed to DMF should be informed about its adverse health effects & trained to avoid skin contact & to use appropriate protective equipment & work practices. Employees should institute engineering controls to ensure that DMF exposure does not exceed the NIOSH recommended exposure limit/OSHA permissible exposure limit of 10 ppm as an 8 hr time-weighted average. NIOSH/OSHA recommend maximum concns for various respirator uses at 100 ppm & above. Eye exposure should be followed by immediate saline irrigations & an ophthalmology review. Skin exposure is followed by prompt water flushing. Oral ingestion of DMF should be treated supportively in a hospital. Liver function tests should be obtained within 24 hr & followed weekly.
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. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Breakthrough times greater than one hour reported by (normally) two or more testers for Butyl Rubber (Butyl). Breakthrough times less (usually significantly) two or more testers for Natural rubber (Nat.Rub) Neoprene (neop.), Nitrile rubber (nitrile) and polyvinyl alcohol (PVA). No data for chloride (nitrile/PVC), polyethylene (PE); polyurethane (PU), polyvinyl chloride (PVC) and Viton.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Recommendations for respirator selection. Max concn for use: 100 ppm. Respirator Class(es): Any supplied-air respirator. May require eye protection.
Recommendations for respirator selection. Max concn for use: 250 ppm. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. May require eye protection.
Recommendations for respirator selection. Max concn for use: 500 ppm. Respirator Class(es): Any supplied-air respirator that has a tight-fitting facepiece and is operated in a continuous-flow mode. May require eye protection. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece.
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: 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.
【Octanol/Water Partition Coefficient】
log Kow = -1.01
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Recovering: Burn in soln in flammable solvent in furnace equipped with alkali scrubber. Recovery and recycle is an alternative to disposal for dimethyl formamide (DMF) from fiber spin baths and from PVC /polyvinyl chloride/ reactor cleaning solvents. Recommendable method: Incineration.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Reaction of methyl formate and dimethylamine
From dimethyl amine and formic acid: Mitchell, Reid, J Am Chem Soc 53, 1879, 1931; Brown, J Appl Chem (London) 1, suppl issue no 2, S159 (1951) ... from dimethylamine and hydrogen cyanide: Benneville et al, J Org Chem 21, 772 (1956) ... from HCN and methanol: Fukuoka, Kominami, Chem Tech 1972 (Nov), 640.
Manufactured by the reaction of CO and dimethylamine. The reaction is carried out in the liquid phase using a sodium methoxide catalyst at 110-120 deg C and 350 kPa (3.5 atm).
U.S. Production

(1975) GREATER THAN 4.54X10+5 G (EST)
(1991) 25,000 tons

An antihistamine with anticholinergic properties.

【Sampling Procedures】
NIOSH Method 1004. Analyte: dimethylformamide; Matrix: air; Sampler: solid sorbent tube (silica gel, 150 mg/75 kg); Flow rate: 0.01-1 l/min; Vol: min: 15 l @ 30 mg/cu m, max: 80 l; Sample stability: greater than or equal to 5 days @ 25 deg C.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
Dimethylformamide reached an average level of 2.8 ug/l in the blood of subjects exposed to 21 ppm of the vapor for 4 hr, & was undetectable at 4 hr after the exposure; the metabolite, methylformamide, averaged between 1 & 2 mg/l in the blood & this level was maintained for at least 4 hr after exposure. Maximal blood levels of about 14 & 8 ug/l were observed for dimethylformamide & methylformamide, respectively, at 0 & 3 hr, after a 4 hr exposure to 87 ppm of the vapor. Repeated daily exposures to 21 ppm of dimethylformamide did not result in accumulation of the chemical or its metabolite in blood. /Dimethylformamide and methylformamide/
Eight healthy male subjects were exposed to dimethylformamide (DMF) vapor at a concn of 8.79 + or - 0.33 ppm for 6 hr daily for 5 consecutive days. All urine voided by the subjects was collected from the beginning of the first exposure to 24 hr past the end of the last exposure & each sample was analyzed for monomethylformamide. Monomethylformamide was rapidly eliminated from the body with urine values peaking within a few hours following the end of each exposure period. The mean for the 7 hr (end of exposure) sample was 4.74 mg/ml. [Krivanek ND et al; J Occup Med 20 (3): 179-182 (1978)] PubMed Abstract
The amount of N-methylformamide recovered in the urine represents only 2-6% of the dose of dimethylformamide inhaled. A substantial portion of an absorbed dose of DMF is excreted unchanged in the expired breath. The urinary concn of N-methylformamide is probably the best index of worker exponent dimethylformamide.
... DMF concns in the blood of rats, 24 hr after the oral admin of 200-4000 mg DMF/kg bw /were determined/ & ... mean blood levels ranging from 40 to 1870 mg/liter /were found/. DMF is readily absorbed via inhalation & dermally. Maximal blood & tissue concns were observed in rats up to 3 hr after exposure to 438 & 6015 mg DMF/cu m ... or to 1690 & 6700 mg DMF/cu m. ... At least 0.8 ml of 100% DMF was absorbed through 14 sq cm of exposed skin of the tails of rats in the course of 8 hr, which is equivalent to an absorption rate of about 57 mg/sq cm/8 hr.
24 hr after an ip dose of 14C-DMF in male rats, about 4% of the radioactivity was recovered in the blood,
... DMF & NMF (/N-methylformamide/) (DMF-OH) concns in the blood of rats & dogs after single & repeated respiratory exposure /were studied/. At the highest airborne concn (6015 mg/cu m), DMF was still detectable in the blood of male rats up to 2 days after the end of a 3 hr exposure. At lower concns, DMF levels in the blood decreased rapidly. After 3 hr exposure to 63 mg/cu m or 6 hr exposure to 87 mg/cu m, similar levels of NMF were found in the blood at the end of the periods of exposure, but no NMF was detectable 3 hr after the end of exposure. Only after a 3 hr exposure to a very high concn (6015 mg/cu m) did NMF levels in blood continue to incr for the 2 days following exposure. Blood concns of DMF in male dogs also decreased rapidly following a 6 hr single exposure. However, NMF could be detected in the blood at higher concn & for a longer period of time after exposure.
The transformation & excretion of DMF in rodents is rapid. When 14C-labeled DMF in 0.1 ml saline was injected ip at 6.8 mmol/kg bw in mice, about 83% of the radioactivity was recovered in the urine within 24 hr following injection. Of this amount, only 5% was unchanged DMF & 56% was C-hydroxylated or N-demethylated derivatives. About 18% of the dose was excreted in the form of unknown chemicals.
Percutaneous absorption in vivo was examined ... in two ways, from liquid dimethylformamide and from dimethylformamide vapor. The first was evaluated by dipping one hand into undiluted dimethylformamide for up to 20 min and by the application of 2 mmol dimethy1formamide over an area of 100 sq cm on the forearm (approximately 1.5 mg/sq cm). In both studies, the absorption rate was 9 mg/sq cm/hr.
Percutaneous uptake of dimethy1formamide vapor was evaluated in volunteers exposed to an atmosphere of 50 mg/cu m dimethylformamide for 4 hr, while wearing light clothing and breathing fresh air through masks. The percutaneous uptake of dimethylformamide increased with increasing ambient temperature and humidity and contributed some 13-36% of the urinary N-hydroxymethyl-N-methylformamide excreted during combined inhalation and percutaneous exposure to the same concentration of dimethylformamide vapor.
Serial blood and urine samples were collected from two cynomolgus monkeys of each sex in groups subjected to whole body exposure to atmospheres of 30, 100 or 500 ppm (90, 300 or 1500 mg/cu m) dimethylformamide for 6 hr per day on five days per week for 13 weeks. As was found in rats and mice, there were disproportionate increases in plasma AUC values of 19 to 37 fold in male monkeys and 35 to 54 fold in females as the atmospheric concentrations increased five fold from 100 to 500 ppm. Plasma half lives ranged from 1 2 hr for dimethylformamide and 4 15 hr for 'N-methylformamide'. There was rapid metabolism, the plasma 'N-methylfomamide' concentration being higher than that of dimethylformamide at 0.5 hr. N-(Hydroxymethyl)-N-methy1formamide formed 56 95% of the urinary metabolites, depending upon the exposure level and duration of the study.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a log Kow of -1.01(2) and a regression-derived equation(3), indicates that dimethylformamide is expected to have very high mobility in soil(SRC). Volatilization of dimethylformamide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.4X10-8 atm-cu m/mole(4). The potential for volatilization of dimethylformamide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 3.9 mm Hg(5). Dimethylformamide rapidly degrades in water and is expected to degrade in soil(SRC). For example, an aerobic unacclimated and acclimated river die-away test showed that dimethylformamide at an initial concn of 30 mg/l completely disappeared within 6 and 3 days, respectively(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a log Kow of -1.01(2), indicates that dimethylformamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 7.4X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An aerobic unacclimated and acclimated river die-away test showed that dimethylformamide at an initial concn of 30 mg/l completely disappeared within 6 and 3 days, respectively(7). However, 24 to 48 hours was required before any degradation was observed among unacclimated samples(7). Thus, dimethylformamide is expected to rapidly degrade in aqueous systems(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethylformamide, which has a vapor pressure of 3.87 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase dimethylformamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 hours(SRC), calculated from its rate constant of 18X10-12 cu cm/molecule-sec at 25 deg C(SRC) determined using a structure estimation method(3).

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