N,N-Dimethylacetamide
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N,N-Dimethylacetamide
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CAS No:
127-19-5
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Formula:
C4H9NO
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Chemical Name:
N,N-Dimethylacetamide
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Synonyms:
Acetic acid dimethylacetamide;N,N-Dimethylacetamide, 99%, pure;N,N-Dimethylacetamide, 99+%, for spectroscopy;N,N-Dimethylacetamide, 99+%, extra pure;N,N-DiMethylacetaMide, for spectroscopy, 99+% 250ML;N,N-DiMethylacetaMide, pure, 99% 1LT;N,N-DIMETHYLACETAMIDE, ANHYDROUS, 99.8%&;N,N-DIMETHYLACETAMIDE, FOR HPLC
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CAS No:
Description
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.
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.
Dimethylacetamide occurs as a clear, colorless, slightly hygroscopic liquid with a weak ammonia-like or fish-like odor. odor threshold concentration is 46.8 ppmv (Leonardos et al., 1969). It is soluble in a wide variety of solvents.
ChEBI: N,N-dimethylacetamide is a member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively.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. It has a role as a human metabolite. It is a member of acetamides and a monocarboxylic acid amide. It is functionally related to an acetamide.
Dimethylacetamide appears as 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.
Characteristics
λ: 270 nm Amax: 1.00λ: 280 nm Amax: 0.30λ: 290 nm Amax: 0.15λ: 310 nm Amax: 0.05λ: 320 nm Amax: 0.03λ: 360-400 nm Amax: 0.01
0.937 g/mL at 25 °C (lit.)
-20 °C (lit.)
164.5-166 °C (lit.)
n20/D1.439(lit.)
miscible
40 mm Hg ( 19.4 °C)
3.89 (vs air)
LD50 orally in rats: 5.4 ml/kg (Bartsch)
Faint ammonia odor
4 (200g/l, H2O, 20℃)
-0.41±0.70(Predicted)
Water soluble.
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.
914 °F
Store below +30°C.
Safety Information
T
16-24-53-45-36-28-26
AB7700000
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.
11-20/22-61-20/21-36
Dimethylacetamide is incompatible with carbon tetrachloride, oxidizing agents, halogenated compounds, and iron. It attacks plastic and rubber. Contact with strong oxidizers may cause fire.
N,N-Dimethylacetamide is combustible.
Toxicity
NIOSH REL: TWA 10 ppm (35 mg/m3), IDLH 300 ppm; OSHA PEL: TWA 10 ppm; ACGIH TLV: TWA 10 ppm (adopted).
Drug Information
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.
N,N-Dimethylacetamide Use and Manufacturing
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.
N,N-dimethylacetamide is an excellent solvent and often acts as a catalyst in halogenation, cyclization, and alkylation reactions. It is an important industrial solvent for polyacrylonitrile, vinyl resins, cellulose derivatives, styrene polymers and linear polyesters. It is also used in all analytical laboratories as a major component of mobile phase in High Performance Liquid Chromatography (HPLC) and in Liquid Chromatography - Mass Spectrometry (LC-MS). N,N-dimethylacetamide lithium chelate complexes intercalate cationic sites in layered silicates.
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