m-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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10589 ;
ChemSpider	7140 ;
ECHA InfoCard	100.002.476
EC Number	247-107-0;
KEGG	C07211 ;
PubChem CID	7418;
UNII	1UA7K8EEXT ;
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) 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/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)
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). verify (what is ?) 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

^ M-TOLUIC ACID - Compound Summary, PubChem.
^ "Dissociation Constants Of Organic Acids And Bases". Retrieved 11 April 2010.
^ Wang, Benjamin J-S. (1974). "An interesting and successful organic experiment (CEC)". J. Chem. Educ. 51 (10): 631. doi:10.1021/ed051p631.2.
^ 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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[1] M-TOLUIC ACID - Compound Summary, PubChem.

[pkaValues-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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