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Properties of substance:

itaconic acid

Synonyms:

1-propene-2,3-dicarboxylic acid

Group of substances:

organic

Physical appearance:

rhombic crystals

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

C5H6O4

Structural formula as text:

HOOCC(=CH2)CH2COOH

Molar/atomic mass: 130.11

Melting point (°C):

167-168

Solubility (g/100 g of solvent):

1,4-dioxane: soluble [Ref.]
acetone: soluble [Ref.]
benzene: sparingly soluble [Ref.]
carbon disulphide: sparingly soluble [Ref.]
chloroform: sparingly soluble [Ref.]
diethyl ether: sparingly soluble [Ref.]
ethanol: soluble [Ref.]
ligroin: sparingly soluble [Ref.]
methanol: soluble [Ref.]
petroleum ether: sparingly soluble [Ref.]
tetrahydrofuran: soluble [Ref.]
water: 5.57 (10°C) [Ref.]
water: 7.68 (20°C) [Ref.]

Reactions:

  1. Yeild 20%. [Ref.1]
    BrC6H4N2Cl + H2C=C(COOH)CH2COOH → BrC6H4CH2C(COOH)=CH2 + CO2 + N2 + HCl
  2. Yeild 18%. [Ref.1]
    O2NC6H4N2Cl + H2C=C(COOH)CH2COOH → O2NC6H4CH2C(COOH)=CH2 + CO2 + N2 + HCl

Dissociation:

pKa (1) = 3.85 (25°C, water)
pKa (2) = 5.45 (25°C, water)

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-466
  2. Dictionary of organic compounds. - Vol. 2, Eccaine - Myrtillin chloride. - London, 1946. - pp. 473
  3. Yalkowsky S.H., Yan H., Jain P. Handbook of aqueous solubility data. – 2nd ed. - CRC Press, 2010. - pp. 147
  4. Химическая энциклопедия. - Т. 2. - М.: Советская энциклопедия, 1990. - pp. 276 [Russian]
  5. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 228 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru