Acetamide

Title: Acetamide
CAS Registry Number: 60-35-5
Additional Names: Acetic acid amide
Molecular Formula: C2H5NO
Molecular Weight: 59.07
Percent Composition: C 40.67%, H 8.53%, N 23.71%, O 27.09%
Line Formula: CH3CONH2
Literature References: Prepd by fractional distillation of ammonium acetate: Coleman, Alvarado, Org. Synth. coll. vol. I, 3 (2nd ed., 1941); Gattermann-Wieland, Praxis des Organischen Chemikers (40th ed., 1961) p 118; Vogel, Practical Organic Chemistry (3rd ed., 1959) p 401. Prepn from methyl acetate, W. P. Munro et al., US 2106697 (1936 to Calco Chem.); from ethyl acetate, Vogel, op. cit., p 403. Studies of acetamide as an ionizing solvent: Jauder, Winkler, J. Inorg. Nucl. Chem. 9, 24, 32, 39 (1959). Toxicological study: Weisburger et al., Toxicol. Appl. Pharmacol. 14, 163 (1969).
Properties: Deliquescent hexagonal crystals. Odorless when pure, but frequently has a mousy odor. d420 1.159. mp 81°. bp760 222°; bp100 158°; bp40 136°; bp20 120°; bp10 105°; bp5 92°. nD78 1.4274. Neutral reaction. pKb (25°): 14.51. One gram dissolves in 0.5 ml water, 2 ml alcohol, 6 ml pyridine. Sol in chloroform, glycerol, hot benzene.
Melting point: mp 81°
Boiling point: bp760 222°; bp100 158°; bp40 136°; bp20 120°; bp10 105°; bp5 92°
pKa: pKb (25°): 14.51
Index of refraction: nD78 1.4274
Density: d420 1.159
Use: Solvent; molten acetamide is an excellent solvent for many organic and inorganic compounds. Solubilizer; renders sparingly soluble substances more soluble in water by mere addition or by fusion. Plasticizer; stabilizer. Manuf methylamine, denaturing alcohol. In organic syntheses.
Acetamidine Hydrochloride Acetamidoeugenol Acetaminosalol Acetanilide Acetarsone

Acetamide
Acetamide skeletal.svg Acetamide-3D-balls.png
Identifiers
CAS number 60-35-5 YesY
PubChem 178
ChemSpider 173 YesY
UNII 8XOE1JSO29 YesY
EC number 200-473-5
DrugBank DB02736
KEGG C06244 YesY
ChEBI CHEBI:27856 YesY
ChEMBL CHEMBL16081 YesY
RTECS number AB4025000
Jmol-3D images Image 1
Properties
Molecular formula C2H5NO
Molar mass 59.07 g mol−1
Appearance colorless, hygroscopic
Odor odorless
mouse-like wit impurities
Density 1.159 g/cm³
Melting point 79 to 81 °C; 174 to 178 °F; 352 to 354 K
Boiling point 221.2 °C; 430.2 °F; 494.3 K (decomposes)
Solubility in water 2000 g L-1[1]
Solubility ethanol 500 g L-1[1]
pyridine 166.67 g L-1[1]
soluble in chloroform, glycerol, benzene[1]
log P -1.26
Vapor pressure 1.3 Pa
Refractive index (nD) 1.4274
Viscosity 2.052 cP (91 °C)
Structure
Crystal structure trigonal
Hazards
MSDS External MSDS
EU Index 616-022-00-4
EU classification Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
NFPA 704.svg
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Flash point 126 °C; 259 °F; 399 K
LD50 700 mg/kg (rat, oral)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acetamide (IUPAC: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.[2] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide.