M-Toluic acid

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.

m-Toluic acid^[1]

Names
Preferred IUPAC name 3-Methylbenzoic acid
Other names meta-Toluic acid m-Methylbenzoic acid meta-Methylbenzoic acid
Identifiers
CAS Number	99-04-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:10589 N
ChemSpider	7140 N
ECHA InfoCard	100.002.476
EC Number	247-107-0
KEGG	C07211 N
PubChem CID	7418
UNII	1UA7K8EEXT Y
CompTox Dashboard (EPA)	DTXSID1021617
InChI 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
SMILES CC1=CC=CC(=C1)C(=O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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.