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Properties of substance:

malonic acid

Group of substances:

organic

Physical appearance:

colorless triclinic crystals

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

C3H4O4

Structural formula as text:

CH2(COOH)2

Molar/atomic mass: 104.06

Melting point (°C):

135.6

Decomposition temperature (°C):

140

Solubility (g/100 g of solvent):

1-propanol: 24.2 (-18.5°C) [Ref.]
1-propanol: 32.1 (0°C) [Ref.]
1-propanol: 44.3 (19.5°C) [Ref.]
ammonia liquid : insoluble [Ref.]
benzene: 0.0014 (25°C) [Ref.]
diethyl ether: 5.7 (5°C) [Ref.]
ethanol: 57 (20°C) [Ref.]
formic acid 95%: 22.42 (19.5°C) [Ref.]
i-butanol: 21.2 (0°C) [Ref.]
i-butanol: 26.9 (19°C) [Ref.]
methanol: 89.8 (0°C) [Ref.]
methanol: 114.1 (19.5°C) [Ref.]
pyridine: 14.6 (26°C) [Ref.]
water: 61.1 (0°C) [Ref.]
water: 73.5 (20°C) [Ref.]
water: 92.5 (50°C) [Ref.]

Numerical data:

Year of discovery: 1858

Density:

1.631 (15°C, g/cm3)
1.619 (16°C, g/cm3)

Reactions:

  1. Yeild 58-60%. [Ref.1]
    CH2(COOH)2 + 2CH2=C(CH3)2 → CH2(COOC(CH3)3)2
  2. Yeild 70-85%. [Ref.1aster]
    CH3O(HO)C6H3CHO + CH2(COOH)2 → CH3O(HO)C6H3CH=CHCOOH + CO2 + H2O
  3. Yeild 78-84%. [Ref.1]
    CH3OC6H4CHO + CH2(COOH)2 → CH3OC6H4CH=CHCOOH + H2O + CO2
  4. Yeild 46%. [Ref.1, Ref.2]
    CH2(COOH)2 + HN3 → NH2CH2COOH + N2 + CO2
  5. Yeild 88%. [Ref.1]
    CH2(COOH)2 + 2CH3OCHCl2 → CH2(COCl)2 + 2HCOOCH3 + 2HCl

Dissociation:

pKa (1) = 2.86 (25°C, water)
pKa (2) = 5.7 (25°C, water)

Dipole moment (D):

2.57 (20°C)

Heat of combustion (kJ/mol):

866.9

LD50 (mg/kg):

1310 (rats, oral)
1500 (rats, intraperitoneal)
4000 (mice, oral)
300 (mice, intraperitoneal)

References:

  1. Journal of Chemical Thermodynamics. - 1987. - Vol. 19. - pp. 317-320
  2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 166-168
  3. Stahl P.H., Wermuth C.G. Handbook of Pharmaceutical Salts: Properties, Selection, and Use. - Wiley-VCH, 2002. - pp. 293
  4. Yalkowsky S.H., Yan H., Jain P. Handbook of aqueous solubility data. – 2nd ed. - CRC Press, 2010. - pp. 51
  5. Мономеры для поликонденсации. - М.: Мир, 1976. - pp. 25-30 [Russian]
  6. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 157, 222 [Russian]
  7. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 387-388 [Russian]
  8. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1133, 1268-1269 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru