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m-Toluic acid

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m-Toluic acid
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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.476 Edit this at Wikidata
EC Number
  • 247-107-0
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)Key: GPSDUZXPYCFOSQ-UHFFFAOYSA-N
SMILES
  • CC1=CC=CC(=C1)C(=O)O
Properties
Chemical formula C8H8O2
Molar mass 136.15 g/mol
Density 1.05 g/cm, 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)
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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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