| Identification | More | [Name]
N,N-Dimethylacetamide | [CAS]
127-19-5 | [Synonyms]
1,2-DICHLOROPROPANE
PROPYLENE CHLORIDE
PROPYLENE DICHLORIDE
Acetyldimeethylamine
CBC 510337
CH3CON(CH3)2
dimethylacetamid
dimethylacetoneamide
Dimethylamid kyseliny octove
Dimethylamide acetate
dimethylamideacetate
dimethylamidkyselinyoctove
Hallucinogen
n,n-dimethyl-acetamid
n,n-dimethylacetamidesolution(40%orless)
N,N-Dimethylethanamide
NSC 3138
nsc3138
SK 7176
Acetic acid dimethylacetamide | [EINECS(EC#)]
201-152-2 | [Molecular Formula]
C4H9NO | [MDL Number]
MFCD00000868 | [Molecular Weight]
87.12 | [MOL File]
127-19-5.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid with a faint ammonia odour | [Melting point ]
-20 °C (lit.) | [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.)
| [Fp ]
158 °F | [storage temp. ]
0-6°C | [solubility ]
>1000g/l soluble | [form ]
Liquid | [pka]
-0.41±0.70(Predicted) | [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 | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [explosive limit]
1.7-11.5%(V) | [Odor Threshold]
0.76ppm | [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 | [Dielectric constant]
37.8（25℃） | [Exposure limits]
NIOSH REL: TWA 10 ppm (35 mg/m3), IDLH 300 ppm; OSHA PEL: TWA 10
ppm; ACGIH TLV: TWA 10 ppm (adopted). | [InChIKey]
FXHOOIRPVKKKFG-UHFFFAOYSA-N | [LogP]
-0.77 at 25℃ | [CAS DataBase Reference]
127-19-5(CAS DataBase Reference) | [IARC]
2B (Vol. 123) 2020 | [NIST Chemistry Reference]
Acetamide, N,N-dimethyl-(127-19-5) | [EPA Substance Registry System]
127-19-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R11:Highly Flammable.
R20/22:Harmful by inhalation and if swallowed .
R61:May cause harm to the unborn child.
R20/21:Harmful by inhalation and in contact with skin .
R36:Irritating to the eyes. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S24:Avoid contact with skin .
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RTECS ]
AB7700000 | [F ]
3-10 | [Autoignition Temperature]
914 °F | [HS Code ]
29241900 | [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 | [Hazardous Substances Data]
127-19-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 5.4 ml/kg (Bartsch) | [IDLA]
300 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetic acid-->Acetyl chloride-->Dimethylamine-->Sodium acetate trihydrate-->CARBON MONOXIDE-->Trimethylamine-->Bromide-->5-(Acetamido)-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide-->Chemical equipment | [Preparation Products]
4-Fluoroaniline-->Diphenylacetylene-->Molosultap-->Cefotaxime sodium-->Fluoxetine-->cis-DL-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid-->4-Methoxy-N,6-dimethyl-1,3,5-triazin-2-amine-->6-(Bromomethyl)-2,4-pteridinediamine hydrobromide-->Flufenamic acid-->1H-PYRROLO[2,3-B]PYRIDINE, 2-METHYL--->Cefoperazone-->3-(Benzofuran-2-yl)-3-oxopropanenitrile ,97%-->1-Chloro-2-propanol-->Cefmenoxime-->4-Hydroxyindole-->Pergolide-->complex polystyrene high efficiency anticorrosion paint-->1-METHYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID-->Cefdinir-->2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE-->2-Acetylbenzofuran-->Phenformin-->2-Acetyl pyrrole-->3-METHYLADENINE-->1,2-Dichloropropane-->1,3-Dichloropropene-->2-ACETYL-3-AMINOTHIOPHENE-->4'-Phenoxyacetophenone-->2-Acetylbenzo[b]thiophene-->1-(5-NITRO-3-THIENYL)ETHAN-1-ONE-->1-Naphthalenesulfonyl chloride-->5-Acetylindole-->CHROMONE-3-CARBOXALDEHYDE-->main chain liquid crystalling polysiloxane polyurethane-->Thiocyclam hydrogen oxalate |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
DIMETHYLACETAMIDE(127-19-5) is an amide. Incompatible with oxidizing agents and halogenated compounds. Exothermic reactions occur with carbon tetrachloride and hexachlorocyclohexane. DIMETHYLACETAMIDE(127-19-5) can react violently in the presence of iron. Special Hazards of Combustion Products: Emits carbon oxides, nitrogen oxides, and dimethylamine when heated to decomposition. | [Air & Water Reactions]
Water soluble. | [Health Hazard]
Liquid causes mild irritation of eyes and skin. Ingestion causes depression, lethargy, confusion and disorientation, visual and auditory hallucinations, perceptual distortions, delusions, emotional detachment, and affective blunting. | [Fire Hazard]
This chemical is combustible. | [Description]
Dimethylacetamide (DMAC) is a synthetic organic compound
that is produced from a reaction of dimethylamine and acetic
acid or acetic anhydride. It is a colorless to yellow liquid with
a faint odor resembling ammonia. DMAC has similar density
to water and is miscible with water and organic substances. This
organic compound is commonly associated with many industrial
uses, either as a starting material or an intermediate.
DMAC is a good solvent that is used in polymer dissolution,
especially in the fiber industry. Historically, DMAC was also
tested as a possible antineoplastic agent in a phase 1 study
involving 17 patients. However, liver and central nervous
system (CNS) toxicity associated with DMAC was observed and
these patients had altered mental states, resulting in no further
drug development. | [Physical properties]
Clear, colorless liquid with a weak, ammonia-like odor. Odor threshold concentration is 46.8 ppmv
(Leonardos et al., 1969). | [Application]
N,N-Dimethylacetamide is primarily used as an industrial solvent and intermediate in the manufacture of pharmaceuticals, fine chemicals, agrochemicals, polymers, and resins. It is also used as a spinning solvent in the production of fibers of various polymers, including acrylic, polyurethane, polyurea copolymer, and meta-aramid. Moreover, this aprotic dipolar solvent is also used in X-ray and photographic products and in the production of polyimide films. The polyimide films are produced for a variety of industries, including consumer electronics, solar photovoltaic and wind energy, aerospace, automotive, and industrial applications. N,N-Dimethylacetamide has other minor uses, including removal of ink, stripping of paint, and also for laboratory use. | [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. | [Preparation]
N,N-Dimethylacetamide is prepared by reaction of dimethylamine with acetic acid, acetic anhydride, or acetate esters. Heating dimethylamine acetate with, or without a catalyst affords N,N-Dimethylacetamide. Reaction of dimethylamine with acetate esters requires a catalyst; sodium methoxide is typically used. | [Production Methods]
Dimethylacetamide is manufactured from acetic acid and dimethylamine in a closed system. | [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]
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 | [Potential Exposure]
Drug,Mutagen; Reproductive Effector; Primary Irritant.Dimethylacetamide is used primarily as a solvent for synthetic and natural resins, especially acrylic fibers and spandex. About 15% of dimethylacetamide production is used tomake alkyl (C12-14) dimethylamine oxide (a surfactant) andrubber chemicals. Dimethylacetamide is also used as anextraction solvent for butadiene manufacture. | [First aid]
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPRif heart action has stopped. Transfer promptly to amedical facility. When this chemical has been swallowed,get medical attention. Give large quantities of water andinduce vomiting. Do not make an unconscious personvomit. | [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. | [Shipping]
This material is not covered in DOT’sPerformance-Oriented Packaging Standards. It may,however, be classified as a combustible liquid, n.o.s. Thisclass requires no shipping label. It falls in Hazard Class 3[each reference to a Class 3 material is modified to read“COMBUSTIBLE LIQUID” when that material is reclassified in accordance with y173.150 (e) or (f) of this subchapter or has a flash point above 60.5℃/141°F but below93℃/200°F] and Packing Group III. The symbol “D” identifies proper shipping names which are appropriate fordescribing materials for domestic transportation but may beinappropriate for international transportation under the provisions of international regulations (e.g., IMO, ICAO). Analternate proper shipping name may be selected when eitherdomestic or international transportation is involved. | [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.] | [Toxicity evaluation]
Little data on the metabolism of DMAC are available in the
literature. Hepatotoxicity of DMAC is believed to be metabolism
dependent. From its metabolic activation (by cytochrome
P450s and probably CYP2E1), reactive species and free radical
metabolites are produced and readily attack the heme prosthetic
group of the liver, leading to suicidal hepatic enzyme
inactivation. | [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. |
| Questions And Answer | Back Directory | [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]
N,N-Dimethylacetamide (DMA) is a transparent colorless liquid. The organic solvent can be mixed with any water, alcohol, ether, ester, benzene, chloroform, and aromatic compounds. It has a very good solvency for many resins and polymers. It is used in the production of acrylic fibers, films, sheets, and coatings, and as a reaction medium and intermediate in organic syntheses. | [Uses]
N,N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide. It is also used as a solvent for fibers like polyacrylonitrile, spandex, as an excipient in drugs viz. vumon, busulfex and in the adhesive industry. It finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers. It is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins. It plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products. It is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings. | [Production method]
Dimethylacetamide has been produced by the reaction of acetic acid with dimethylamine (Siegle, 1980).
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