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Properties of substance:

2-nitroaniline

Group of substances:

organic

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

C6H6N2O2

Structural formula as text:

H2NC6H4NO2

Molar/atomic mass: 138.13

Melting point (°C):

71

Boiling point (°C):

284

Solubility (g/100 g of solvent):

acetone: 158.5 (25°C) [Ref.]
ammonia liquid : 15 (20°C) [Ref.]
benzene: 27.42 (23.2°C) [Ref.]
carbon tetrachloride: 1.18 (20°C) [Ref.]
chloroform: 11.17 (0°C) [Ref.]
chloroform: 27.83 (20°C) [Ref.]
ethanol abs.: 27.87 (25°C) [Ref.]
m-xylene: 11.59 (15°C) [Ref.]
p-cymene: 6.33 (30°C) [Ref.]
water: 0.08932 (20°C) [Ref.]

Synthesis 1:

Reference: Euklid Sakellarios. Uber ein bequemes Verfahren zur Darstellung des o-Nitro-anilins im Laboratorium. (Bearbeitet von Demosthenes Jatrides.) / Chemische Berichte. - 1925. - Vol. 58, No. 10 pp. 2288 [doi: 10.1002/cber.19250581008]

299 g (1 mole) of potassium 4-acetamido-3-nitrobenzenesulfonate is dissolved in 1500 cc. of 67% sulfuric acid and refluxed for 1 hour. The clear solution is poured into ice water, and the precipitate of o-nitroaniline is collected on a Buchner funnel.

The mother liquors are neutralized with calcium carbonate and then with ammonia. An additional amount of o-nitroaniline is steam-distilled from the liquours and added to the main batch of the product. The total yield is 110 g, corresponding to 80% of the theory.

Dissociation:

pKBH+ (1) = -0.29 (25°C, water)

LD50 (mg/kg):

3520 (white rats, )

References:

  1. Dean J.A. Lange's handbook of chemistry. - 1999. - pp. 1.282
  2. Olah G.A., Prakash G.K.S., Molnar A., Sommer J. Superacid chemistry. - 2ed. - Wiley, 2009. - pp. 14
  3. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 400-403
  4. Urbanski T. Chemistry and technology of explosives. - vol.1. - Warszawa, 1964. - pp. 556-557
  5. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 250
  6. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 440-441, 908 [Russian]
  7. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1275, 1456-1457 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru