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Properties of substance:

4-aminobenzenesulfonamide

Synonyms:

prontosil album
sulfanilamide

Group of substances:

organic

Physical appearance:

white crystals

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

C6H8N2O2S

Structural formula as text:

H2NC6H4SO2NH2

Molar/atomic mass: 172.205

Melting point (°C):

165

Solubility (g/100 g of solvent):

acetone: very soluble [Ref.]
chloroform: practically insoluble [Ref.]
diethyl ether: practically insoluble [Ref.]
ethanol: 2.9 (20°C) [Ref.]
methanol: soluble [Ref.]
water: 0.1996 (1°C) [Ref.]
water: 0.4 (15°C) [Ref.]
water: 0.6 (20°C) [Ref.]
water: 1.088 (31°C) [Ref.]
water: 1.5 (37°C) [Ref.]
water: 9.747 (79°C) [Ref.]

Density:

1.08 (25°C, g/cm3)

Reactions:

  1. Yeild 88%. [Ref.1aster]
    H2NC6H4SO2NH2 + NaNO2 + 2HCl → H2NSO2C6H2N2Cl + NaCl + 2H2O
    H2NSO2C6H2N2Cl + 2SnCl2 + 4HCl → H2NSO2C6H2NHNH3Cl + 2SnCl4

Dissociation:

pKBH+ (1) = 10.43 (25°C, water)

LD50 (mg/kg):

3900 (rats, oral)
1400 (rats, intravenous)
3000 (mice, oral)
500 (mice, intravenous)
2000 (dogs, oral)

References:

  1. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 3-14
  2. Clarke's isolation and identification of drugs. - 2ed. - London: Pharmaceutical press, 1986. - pp. 991
  3. Kleemann A. Pharmaceutical Substances. - 2000. - pp. 1934-1935
  4. The Merck Index 11th ed., Merck & Company, 1989. - pp. 1408-1409
  5. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 273-274
  6. Беликов В.Г. Учебное пособие по фармацевтической химии. - М.: Медицина, 1979. - pp. 198 [Russian]
  7. Краткая химическая энциклопедия. - Т. 4: Пирометаллургия-С. - М.: Советская энциклопедия, 1965. - pp. 1073-1074 [Russian]
  8. Машковский М.Д. Лекарственные средства. - 13-е изд., Т. 2. - Харьков: Торсинг, 1997. - pp. 294-295 [Russian]
  9. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 450 [Russian]
  10. Справочник химика. - Т. 2. - Л.-М.: Химия, 1964. - pp. 962-963 [Russian]
  11. Сьютер Ч. Химия органических соединений серы. - Ч. 3. - М.: ИИЛ, 1951. - pp. 33-36 [Russian]
  12. Халецкий А.М. Фармацевтическая химия. - Л.: Медицина, 1966. - pp. 262-265 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru