m-Toluic acid[1]
Skeletal formula of m-toluic acid
Ball-and-stick model of the m-toluic acid molecule
Names
Preferred IUPAC name
3-Methylbenzoic acid
Other names
meta-Toluic acid
m-Methylbenzoic acid
meta-Methylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.476
EC Number
  • 247-107-0
KEGG
UNII
  • InChI=1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10) ☒N
    Key: GPSDUZXPYCFOSQ-UHFFFAOYSA-N ☒N
  • CC1=CC=CC(=C1)C(=O)O
Properties
C8H8O2
Molar mass 136.15 g/mol
Density 1.05 g/cm3, solid
Melting point 111 to 113 °C (232 to 235 °F; 384 to 386 K)
Boiling point 263 °C (505 °F; 536 K)
Acidity (pKa) 4.27 (in water)[2]
Hazards
Safety data sheet (SDS) External MSDS
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

m-Toluic acid, (IUPAC: 3-methylbenzoic acid), is an aromatic carboxylic acid, with formula (CH3)C6H4(COOH). It is an isomer of p-toluic acid and o-toluic acid.

Preparation

m-toluic acid is often prepared in the laboratory by refluxing m-xylene with either nitric acid or potassium permanganate, oxidizing one of the methyl groups to COOH.

Uses

It serves, among other purposes, as a precursor to DEET (N,N-diethyl-m-toluamide), the well-known insect repellent.[3][4]

References

  1. ↑ M-TOLUIC ACID - Compound Summary, PubChem.
  2. ↑ "Dissociation Constants Of Organic Acids And Bases". Retrieved 11 April 2010.
  3. ↑ Wang, Benjamin J-S. (1974). "An interesting and successful organic experiment (CEC)". J. Chem. Educ. 51 (10): 631. doi:10.1021/ed051p631.2.
  4. ↑ Donald L. Pavia (2004). Introduction to organic laboratory techniques (Google Books excerpt). Cengage Learning. pp. 370–376. ISBN 978-0-534-40833-6.


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