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Properties of substance:

3-methylbenzoic acid

Synonyms:

m-toluic acid
meta-toluic acid

Group of substances:

organic

Physical appearance:

colorless prismatic crystals

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

C8H8O2

Structural formula as text:

CH3C6H4COOH

Molar/atomic mass: 136.148

Melting point (°C):

112

Boiling point (°C):

263

CAS №: 99-04-7

Solubility (g/100 g of solvent):

chloroform: sparingly soluble [Ref.]
diethyl ether: very soluble [Ref.]
ethanol: very soluble [Ref.]
m-xylene: 9.37 (14°C) [Ref.]
monochlorbenzene: 9.22 (14.1°C) [Ref.]
p-xylene: 11.51 (14°C) [Ref.]
water: 0.098 (25°C) [Ref.]
water: 1.17 (80°C) [Ref.]

Not numerical data:

volatile in steam

Density:

1.054 (112°C, g/cm3)

Synthesis 1:

Reference: Tomisek, A., Graham, B., Griffith, A., Pease, C. S., & Christensen, B. E. Syntheses of Certain 8-Nitroquinolines / Journal of the American Chemical Society. - 1946. - Vol. 68, No. 8 pp. 1588 [doi: 10.1021/ja01212a063]


2CH3C6H4CN + 4H2O + H2SO4 → 2CH3C6H4COOH + (NH4)2SO4

A mixture consisting of 100 cc. of water, 100 cc. of concentrated sulfuric acid and 45 g. of m-tolunitrile was refluxed for four hours and then diluted with 100 cc. of water, which was added through the top of the condenser. The flask was stoppered and shaken under a cold water tap until the oily layer solidified as granules. After further cooling with ice, the granules were removed by filtration, dissolved in base and reprecipitated with concentrated hydrochloric acid. The cooled mixture was then filtered arid washed twice with water. A yield of 50.3 g. (96%) of m-toluic acid with m. p. 108.5—111° was obtained.

Dissociation:

pKa (1) = 4.27 (25°C, water)

LD50 (mg/kg):

1630 (white mice, )

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-514
  2. Dictionary of organic compounds. - Vol. 3, naphthacarbazole - zygadenine. - М.: ИИЛ, 1949. - pp. 777
  3. Journal of Physical and Chemical Reference Data. - 2013. - Vol. 42, No. 3. - pp. 033103-460 - 033103-475
  4. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 586-588
  5. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 475
  6. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 493 [Russian]
  7. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1395 [Russian]
  8. Справочник химика. - Т. 2. - Л.-М.: Химия, 1964. - pp. 994-995 [Russian]
  9. Справочник химика. - Т. 3. - М.-Л.: Химия, 1965. - pp. 94 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru