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(Top) 1 Preparation 2 Uses 3 References

m-Toluic acid

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m-Toluic acid^[1]

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

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

C₈H₈O₂

136.15 g/mol

1.05 g/cm³, solid

111 to 113 °C (232 to 235 °F; 384 to 386 K)

Boiling point

263 °C (505 °F; 536 K)

Acidity (pK_a)

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

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[edit]

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

Uses[edit]

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

References[edit]

^ 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.

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

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