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N,N-Dimethylacetamide

Basic information Outline Chemical Properties Uses Medical Care Test methods Transport requirements Production method Safety Related Supplier

N,N-Dimethylacetamide Basic information

Product Name:
N,N-Dimethylacetamide
CAS:
127-19-5
MF:
C4H9NO
MW:
87.12
EINECS:
204-826-4
Mol File:
127-19-5.mol
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N,N-Dimethylacetamide Chemical Properties

Melting point:
-20 °C
Boiling point:
164.5-166 °C(lit.)
Density 
0.937 g/mL at 25 °C(lit.)
vapor density 
3.89 (vs air)
vapor pressure 
40 mm Hg ( 19.4 °C)
refractive index 
n20/D 1.439(lit.)
Flash point:
158 °F
storage temp. 
0-6°C
solubility 
>1000g/l soluble
pka
-0.41±0.70(Predicted)
form 
Liquid
color 
Colorless to yellowish
Odor
Faint ammonia odor
PH
4 (200g/l, H2O, 20℃)
PH Range
4 at 200 g/l at 20 °C
Relative polarity
6.3
Odor Threshold
0.76ppm
explosive limit
1.7-11.5%(V)
Water Solubility 
miscible
λmax
λ: 270 nm Amax: 1.00
λ: 280 nm Amax: 0.30
λ: 290 nm Amax: 0.15
λ: 310 nm Amax: 0.05
λ: 320 nm Amax: 0.03
λ: 360-400 nm Amax: 0.01
Merck 
14,3227
BRN 
1737614
Exposure limits
NIOSH REL: TWA 10 ppm (35 mg/m3), IDLH 300 ppm; OSHA PEL: TWA 10 ppm; ACGIH TLV: TWA 10 ppm (adopted).
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
FXHOOIRPVKKKFG-UHFFFAOYSA-N
CAS DataBase Reference
127-19-5(CAS DataBase Reference)
NIST Chemistry Reference
Acetamide, N,N-dimethyl-(127-19-5)
IARC
2B (Vol. 123) 2020
EPA Substance Registry System
Dimethylacetamide (127-19-5)
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Safety Information

Hazard Codes 
T
Risk Statements 
11-20/22-61-20/21-36
Safety Statements 
16-24-53-45-36-28-26
RTECS 
AB7700000
3-10
Autoignition Temperature
914 °F
HS Code 
29241900
Hazardous Substances Data
127-19-5(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 5.4 ml/kg (Bartsch)

MSDS

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N,N-Dimethylacetamide Usage And Synthesis

Outline

N,N-Dimethylacetamide is a highly polar aprotic solvent, micro ammonia odor, very strong dissolving power, soluble wide, miscible with water, aromatics, esters, ketones, alcohols, ether, benzene and chloroform and other arbitrary and enable activation of molecular compounds. It is widely used as a solvent and a catalyst. The solvent, with high boiling point, flash point, thermal stability and chemical stability of the solvent, is used for polyacrylonitrile spinning solvent, synthetic resin and natural resins, formic acid vinyl ester resin, vinyl pyridine copolymer and aromatic carboxylic acid. The catalyst can be used in the process of urea heating to produce the reaction of cyanide, sodium halide and metal cyanide to produce the reaction of alkyl acetylene, organic halide and isocyanate. N,N-dimethylacetamide also can be used as electrolytic solvent and photography with coupler solvent, de paint agent, organic synthesis of raw materials, pesticide and pharmaceutical raw materials. Separation of styrene from C8 fraction, extraction, distillation, solvent, etc.

Chemical Properties

Transparent colorless liquid. The organic solvent can be mixed with any water, alcohol, ether, ester, benzene, chloroform, and aromatic compounds.

Uses

  • N,N-Dimethylacetamide (DMAC) is mainly used as synthetic fibers (acrylonitrile) and polyurethane spinning synthetic polyamide resin and a solvent, but also it is used for separating styrene from the C8 fraction extractive distillation solvent, and it is widely used in the aspects of polymer films, coatings and medicine. Currently it is used to synthesize a large number of antibiotics and pesticides in the pharmaceutical and pesticide. The catalyst can also be used for the reaction, electrolytic solvent, paint scavengers and various crystalline solvent adducts and complexes.
  • Used as the reaction solvent of pharmaceutical synthesis, synthetic fiber spinning solvents and synthetic resins, photographic chemicals chromogenic agent solvents, paints and other solvents, catalyst.

Medical Care

When the pre-employment and periodic medical examinations, we should pay special attention to the skin, the central nervous system, liver disease or liver function tests.

Test methods

Measured in the air: adsorption with silica, methanol and analyzed by gas chromatography.

Transport requirements

N,N-dimethylacetamide Department are toxic flammable liquids, adjustment shall be toxic substances provides storage and transportation. Transportation shall be marked "dangerous drugs" mark, and prevent the sun, impact, when handling, attention gently on the container.
Recommended methods of controlling waste incineration (incinerators shall have a scrubber or thermal means to reduce the discharge of NOx).

Production method

Dimethylacetamide has been produced by the reaction of acetic acid with dimethylamine (Siegle, 1980).

Chemical Properties

Dimethylacetamide occurs as a clear, colorless, slightly hygroscopic liquid with a faint ammonia odour. It has a weak ammonia-like or fish-like odor.

Physical properties

Clear, colorless liquid with a weak, ammonia-like odor. Odor threshold concentration is 46.8 ppmv (Leonardos et al., 1969).

Uses

Commercial solvent especially for textile fibers

Uses

Solvent for many organic reactions and in industrial applications. dimethylacetamide is an important industrial solvent for polyacrylonitrile, vinyl resins, cellulose derivatives, styrene polymers and linear polyesters.

Definition

ChEBI: A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.

Production Methods

Dimethylacetamide is manufactured from acetic acid and dimethylamine in a closed system.

General Description

A clear colorless liquid with a faint odor similar to ammonia. About the same density as water. Flash point 145°F. Vapors heavier than air. May by toxic by skin absorption. May irritate eyes and skin.

Air & Water Reactions

Water soluble.

Reactivity Profile

N,N-Dimethylacetamide is an amide. Incompatible with oxidizing agents and halogenated compounds. Exothermic reactions occur with carbon tetrachloride and hexachlorocyclohexane. N,N-Dimethylacetamide can react violently in the presence of iron. Special Hazards of Combustion Products: Emits carbon oxides, nitrogen oxides, and dimethylamine when heated to decomposition.

Health Hazard

A study of 41 workers who had been exposed to dimethylacetamide from 2 to 10 years revealed the occurrence of disorders reflecting liver damage (Corsi, 1971). Retention of bromosulfophthalein was increased in 9 of 10 workers who had been exposed to dimethylacetamide for 7 to 10 years, and in 10 of 20 workers who had been exposed to dimethylacetamide for 2 to 7 years. Other parameters of hepatic function which were altered in the exposed individuals include proteinemia, cholesterolemia, activities of hepatic transaminases and alkaline phosphatase in serum, and bilirubinemia. Hepatomegaly was diagnosed in 14 workers.
In a clinical trial, dimethylacetamide was administered to patients with advanced malignancies and caused abnormal mental states (Weiss et al 1962a, b). This effect was observed at a dose of 400 mg/kg given daily for 3 or more days.
The symptoms were not seen at 300 mg/kg or lower. The second or third dose caused depression, lethargy, occasional confusion or disorientation. The fourth or fifth dose produced striking hallucinations, perceptual distortions and delusions in all nine patients. All patients reverted to normal several days after discontinuation of treatment with dimethylacetamide.

Fire Hazard

N,N-Dimethylacetamide is combustible.

Pharmaceutical Applications

Dimethylacetamide is used as a solvent in oral and injectable pharmaceutical formulations. It has been used as a cosolvent to solubilize poorly soluble drugs. The use of dimethylacetamide has also been investigated as a vehicle for the parenteral delivery of relatively small peptides.
The use of solvents such as dimethylacetamide has been shown to influence the size and rate of release of norfloxacin from nanoparticles.
Dimethylacetamide has also been used in topical formulations and has been evaluated as a permeation enhancer for transdermal drug delivery.

Industrial uses

Dimethylacetamide is a powerful industrial solvent, the uses of which are very similar to those of dimethylformamide (Siegle, 1980). Its strong solvent action renders it particularly useful in the manufacture of films and fibers and as a solvent for polyacrylonitrile, polyvinyl chloride, polyamides, cellulose derivatives and polystyrenes and in coatings and adhesive formulations. Dimethylacetamide dissolves many inorganic salts.

Safety Profile

Moderately toxic by skin contact, inhalation, intravenous, and intraperitoneal routes. Mildly toxic by ingestion. Experimental teratogenic and reproductive effects. A skin and eye irritant. Less toxic than dimethylformamide. Mutation data reported. Combustible when exposed to heat and flame. A moderate explosion hazard. Violent reaction with halogenated compounds (e.g., carbon tetrachloride, hexachlorocyclohexane) when heated above 9OOC. Iron powder catalyzes the reaction so that it initiates at 71OC. When heated to decomposition it emits toxic fumes of NOx

Safety

Dimethylacetamide is used in pharmaceutical preparations as a solvent in parenteral formulations and is generally regarded as a nontoxic material when used as an excipient. Animal toxicity studies indicate that dimethylacetamide is readily absorbed into the bloodstream following inhalation or topical application. Repeated exposure to dimethylacetamide may be harmful and can result in liver damage. High intravenous doses (>400mg/kg/day for 3 days) may be hallucinogenic.
LD50 (rabbit, SC): 9.6g/kg(11) LD50 (rat, IP): 2.75g/kg LD50 (rat, IV): 2.64g/kg LD50 (rat, oral): 4.93g/kg LD50 (mouse, inhalation): 7.2g/kg LD50 (mouse, IP): 2.8g/kg

Carcinogenicity

DMAC was not carcinogenic in rats administered 100, 300, or 1000 mg/kg/day in drinking water for 2 years. Rats and mice were exposed by inhalation to 0, 25, 100, or 350 ppm DMAC for 6 h/day, 5 days/week for 18 months (mice) or 2 years (rats). DMAC was not oncogenic under these conditions in either the rat or the mouse.

Environmental Fate

Chemical/Physical. Releases toxic fumes of nitrogen oxides when heated to decomposition (Sax and Lewis, 1987).

Metabolism

Gas Chromatographie analysis of the urine of rats which had received dimethylacetamide by the subcutaneous route indicated the presence of N-methyl-acetamide and acetamide (Barnes and Ranta, 1972). Both metabolites were also found by the same authors in incubation mixtures of dimethylacetamide with rat liver homogenate. N-Methylacetamide was detected in the urine of human volunteers who had inhaled dimethylacetamide or absorbed dimethylacetamide vapor through the skin (Maxfield et al 1975). Measurement of the amount of the metabolite N-methylacetamide excreted by individuals exposed to dimethylacetamide vapors with or without face masks which allowed the inhalation of air free of dimethylacetamide indicated that more dimethylacetamide was absorbed through the lungs than through the skin. Interestingly, in this study, only 2-10% of the amount of dimethylacetamide inhaled was recovered in the urine in the form of N-methylacetamide. It has been suggested that the major urinary metabolite of the analogous dimethylformamide is N-(hydroxymethyl)-N-methylformamide and not N-methylformamide, since the carbinolamide decomposes on the gas chroma-tography column (to N-methylformamide) but is relatively stable in aqueous solution (Kestell et al 1986). In analogy, it would be logical to assume that the N-methylacetamide found in the urine after exposure to dimethylacetamide really arose from chemical breakdown of N-(hydroxymethyl)-N-methylacetamide during the analytical process. This contention, however, remains to be proven.

storage

Dimethylacetamide should be stored in an airtight container, protected from light, in a cool, dry place. Dimethylacetamide has an almost unlimited shelf-life when kept in closed containers and under nitrogen. It is combustible.

Purification Methods

Shake the amide with BaO for several days, reflux it with BaO for 1hour, then fractionally distil it under reduced pressure. Store it over molecular sieves. [Beilstein 4 IV 180.]

Incompatibilities

Dimethylacetamide is incompatible with carbon tetrachloride, oxidizing agents, halogenated compounds, and iron. It attacks plastic and rubber. Contact with strong oxidizers may cause fire.

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM injections, IV injections and infusions). Included in parenteral medicines licensed in the UK.

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Basic information Outline Chemical Properties Uses Medical Care Test methods Transport requirements Production method Safety Related Supplier