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Properties of substance:

N-phenylacetamide

Synonyms:

acetanilide

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C8H9NO

Structural formula as text:

C6H5NHCOCH3

Molar/atomic mass: 135.2

Melting point (°C):

114.3

Boiling point (°C):

304

Solubility (g/100 g of solvent):

1,1,2-trichloro-1,2,2-trifluoroethane: soluble [Ref.]
1-propanol: 22.6 (20°C) [Ref.]
2-propanol: 25.9 (20°C) [Ref.]
acetic acid 85%: 40.4 (20°C) [Ref.]
acetic acid 85%: 67.9 (35°C) [Ref.]
acetone: 45.24 (30°C) [Ref.]
ammonia liquid : 92.3 (20°C) [Ref.]
amyl alcohol: 16.3 (25°C) [Ref.]
aniline: 24 (30°C) [Ref.]
benzaldehyde: 23.2 (30°C) [Ref.]
benzene: 1.08 (20°C) [Ref.]
benzene: 1.4 (25°C) [Ref.]
benzene: 2.46 (30°C) [Ref.]
benzylamine: soluble [Ref.]
carbon disulphide: 0.23 (25°C) [Ref.]
carbon tetrachloride: 0.102 (25°C) [Ref.]
chloroform: 3.9 (0°C) [Ref.]
chloroform: 13 (20°C) [Ref.]
chloroform: 65 (60°C) [Ref.]
dibutylamine: sparingly soluble [Ref.]
diethyl ether: 2.88 (25°C) [Ref.]
diethylamine: soluble [Ref.]
ethanol 50%: 11.9 (20°C) [Ref.]
ethanol 50%: 18.8 (30°C) [Ref.]
ethanol abs.: 28.8 (20°C) [Ref.]
ethanol abs.: 40.5 (30°C) [Ref.]
formic acid 95%: 103 (16.8°C) [Ref.]
methanol: 46 (20°C) [Ref.]
methanol: 215 (60°C) [Ref.]
n-butylamine: very soluble [Ref.]
nitrobenzene: 7.6 (25°C) [Ref.]
p-cymene: 7.23 (30°C) [Ref.]
phenol: 107 (40°C) [Ref.]
propylene glycol: 2.13 [Ref.]
pyridine: 48.6 (20°C) [Ref.]
quinoline: 12.67 (20°C) [Ref.]
toluene: 0.54 (20°C) [Ref.]
toluene: 1.63 (40°C) [Ref.]
toluene: 8.69 (60°C) [Ref.]
toluene: 74.85 (80°C) [Ref.]
toluene: 355.5 (100°C) [Ref.]
tributylamine: sparingly soluble [Ref.]
triethylamine: sparingly soluble [Ref.]
water: 0.47 (16°C) [Ref.]
water: 0.5015 (20°C) [Ref.]
water: 0.56 (25°C) [Ref.]
water: 0.71 (30°C) [Ref.]
water: 1.309 (50°C) [Ref.]
water: 2.606 (70°C) [Ref.]
xylene: 1.68 (32.5°C) [Ref.]

Properties of solutions:

0,54% (wt.), solvent - water
  Density (g/cm3) = 0.997 (25°)

Density:

1.0261 (20°C, g/cm3)

Synthesis 1:

Reference: Odell, A. F., & Hines, C. W. The pyrosulfates of sodium and potassium as condensing agents / Journal of the American Chemical Society. - 1913. - Vol. 35, No. 1 pp. 83 [doi: 10.1021/ja02190a008]

Thirty grams of glacial acetic acid, 25 grams of aniline and 25 grams of pulverized sodium pyrosulfate are heated in a flask, with an air condenser, in an oil bath at 130—140° for 1 hour. The resulting mass is powdered and boiled with 300 cc. of water until everything dissolves. On cooling, acetanilide of m. p. 113° crystallizes out. The yield is almost quantitative.

Dissociation:

pKBH+ (1) = 0.4 (25°C, water)

LD50 (mg/kg):

800 (rats, oral)
540 (rats, intraperitoneal)
1210 (mice, oral)
500 (mice, intraperitoneal)

References:

  1. Lewis R.J. Sax's Dangerous Properties of Industrial Materials. - 11ed. - Wiley-interscience, 2004. - pp. 13-14
  2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 600-605
  3. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 485-486
  4. Реутов О.А., Курц А.Л., Бутин К.П. Органическая химия. - 2-е изд., Ч.1. - М.: Бином. Лаборатория знаний, 2005. - pp. 222 [Russian]
  5. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 498-499, 910 [Russian]
  6. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1144, 1453, 1515 [Russian]
  7. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 61 [Russian]
  8. Химия и жизнь. - 1990. - №4. - pp. 91 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru