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Properties of substance:

1,3,5,7-tetraazatricyclo[3.3.1]decane



skc-file

Synonyms:

hexamethylenetetramine
hexamine
methenamine
urotropin

Group of substances:

organic

Physical appearance:

colorless rhombic crystals

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

C6H12N4

Structural formula as text:

(CH2)6N4

Molar/atomic mass: 140.19

Melting point (°C):

263

Decomposition temperature (°C):

280

Solubility (g/100 g of solvent):

acetone: 0.82 (20°C) [Ref.]
ammonia liquid : 1.3 (20°C) [Ref.]
amyl alcohol: 2.26 (20°C) [Ref.]
benzene: 0.23 (20°C) [Ref.]
carbon disulphide: 0.13 (20°C) [Ref.]
carbon tetrachloride: 0.53 (20°C) [Ref.]
chloroform: 8.09 (12°C) [Ref.]
chloroform: 9 (20°C) [Ref.]
diethyl ether: 0.08 (20°C) [Ref.]
ethanol: 2.89 (20°C) [Ref.]
ethanol 90%: 5.58 (20°C) [Ref.]
ethanol abs.: 3.22 (12°C) [Ref.]
glycerol 98.5%: 20.5 (20°C) [Ref.]
methanol: 9.18 (20°C) [Ref.]
petroleum ether: insoluble [Ref.]
trichloroethylene: 0.08 (20°C) [Ref.]
water: 81.32 (12°C) [Ref.]
water: 167 (20°C) [Ref.]
xylene: 0.14 (20°C) [Ref.]

Numerical data:

Year of discovery: 1859

Density:

1.331 (-5°C, g/cm3)
1.27 (25°C, g/cm3)

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

-99.2 (s)

Heat of combustion (kJ/mol):

4212

References:

  1. Kaur N., Kishore D. An insight into hexamethylenetetramine: a versatile reagent in organic synthesis / Journal of the Iranian Chemical Society. - 2013. - Vol. 10, No. 6. - pp. 1193-1228
  2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 434
  3. Smolin E.M., Rapoport L. s-Triazines and derivatives. - New York: Interscience Publishers Inc., 1959. - pp. 545-591
  4. The Merck Index 11th ed., Merck & Company, 1989. - pp. 941
  5. Государственная фармакопея СССР. - 10-е изд. - М.: Медицина, 1968. - pp. 351-352 [Russian]
  6. Огородников С.К. Формальдегид. - Л.: Химия, 1984. - pp. 105 [Russian]
  7. Орлова Е.Ю. Химия и технология бризантных взрывчатых веществ. - Л.: Химия, 1973. - pp. 502-503 [Russian]
  8. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 187 [Russian]
  9. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1468 [Russian]
  10. Химическая энциклопедия. - Т. 1. - М.: Советская энциклопедия, 1988. - pp. 507 [Russian]
  11. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 122 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru