N-Methylacetamide Basic information

Product Name: N-Methylacetamide

Synonyms: LABOTEST-BB LT00779190;dimethylcarboxamide;ACETYL METHYLAMIDE;ACETYLMETHYLAMINE;ACETMETHYLAMIDE;ACETIC ACID METHYLAMIDE;NMA;N-METHYLACETAMIDE

CAS: 79-16-3

MF: C3H7NO

MW: 73.09

EINECS: 201-182-6

Product Categories: Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines

Mol File: 79-16-3.mol

N-Methylacetamide Structure

N-Methylacetamide Chemical Properties

Melting point 26-28 °C (lit.)

Boiling point 204-206 °C (lit.)

density 0.957 g/mL at 25 °C (lit.)

refractive index n20/D 1.433(lit.)

Fp 227 °F

storage temp. Inert atmosphere,Room Temperature

solubility miscible with ethanol, ether, acetone, water, chloroform, benzene

pka 16.61±0.46(Predicted)

PH 7 (H2O)

explosive limit 3.2-18.1%(V)

Water Solubility soluble

BRN 1071255

Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey OHLUUHNLEMFGTQ-UHFFFAOYSA-N

CAS DataBase Reference 79-16-3(CAS DataBase Reference)

NIST Chemistry Reference Acetamide, N-methyl-(79-16-3)

EPA Substance Registry System N-Methylacetamide (79-16-3)

Safety Information

Hazard Codes T

Risk Statements 61

Safety Statements 53-45

WGK Germany 2

RTECS AC5960000

TSCA Yes

HS Code 29241900

Hazardous Substances Data 79-16-3(Hazardous Substances Data)

Toxicity LD50 oral in rat: 5gm/kg

MSDS Information

Provider Language

N-Methylacetamide English

SigmaAldrich English

ACROS English

ALFA English

N-Methylacetamide Usage And Synthesis

Chemical Properties colourless liquid or solid

Uses N-Methylacetamide is used as a chemical intermediate in the production of life science, agrochemicals, electronic materials and construction materials. It is also used as a solvent, in electrochemistry.

Definition ChEBI: A monocarboxylic acid amide that is the N-methyl derivative of acetamide.

Production Methods Af-Methylacetamide has been prepared by reaction of methylamine with hot acetic acid (D'Alelio and Reid, 1937) and with acetic anhydride (Mauger and Soper, 1946). Other methods include heating iV,N-dimethylurea with acetic acid (US Patent, 1936) and reduction/hydrogenation of N-(hydroxymethyl)acetamide (US Patent, 1944).

Industrial uses Even though N-methylacetamide shares many general physical and chemical properties with dimethylacetamide, it has not found the extensive industrial applications of the latter. N-methylacetamide dissolves many inorganic salts.

Safety Profile Moderately toxic by intraperitoneal and subcutaneous routes. Mddly toxic by ingestion and intravenous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Metabolism In a recent comparative toxicity and metabolism study on four formamides and on N-methylacetamide, the sole metabolite of N-methylacetamide in the urine of mice was identified as N-(hydroxymethyl)acetamide (Kestell et al 1987). There was no evidence of induction of hepatic drug metabolizing enzymes in rats following treatment with N-methylacetamide (Ackerman and Leibman, 1977). N-Methylacetamide influenced neither the sleeping time induced by hexobarbital nor the metabolism of hexobarbital or aniline.

Purification Methods Fractionally distil it under vacuum, then fractionally crystallise it twice from its melt. Likely impurities include acetic acid, methyl amine and H2O. For a detailed purification procedure, see Knecht and Kolthoff, Inorg Chem 1 195 1962. Although N-methylacetamide is commercially available it is often extensively contaminated with acetic acid, methylamine, water and an unidentified impurity. The recommended procedure is to synthesise it in the laboratory by direct reaction. The gaseous amine is passed into hot glacial acetic acid, to give a partially aqueous solution of methylammonium acetate which is heated to ca 130o to expel water. Chemical methods of purification such as extraction by pet ether, treatment with H2SO4, K2CO3 or CaO can be used but are more laborious. Tests for purity include the Karl Fischer titration for water; this can be applied directly. Acetic acid and methylamine can be detected polarographically. In addition to the above, purification of N-methylacetamide can be achieved by fractional freezing, including zone melting, repeated many times, or by vacuum distillation under reduced pressures. For details of zone melting techniques, see Knecht in Recommended Methods for Purification of Solvents and Tests for Impurities, Coetzee Ed. Pergamon Press 1982.[Beilstein 4 IV 176.]

N-Methylacetamide Preparation Products And Raw materials

Raw materials N,N-Dimethylacetamide

Preparation Products Tirofiban-->1,4-DICYANONAPHTHALENE-->7-Hydroxyisoflavone