M-Toluic acid
{{DISPLAYTITLE:m-Toluic acid}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447860534
| Name = m-Toluic acid
| ImageFileL1 = 3-toluic acid.svg
| ImageSizeL1 = 125
| ImageAltL1 = Skeletal formula of m-toluic acid
| ImageFileR1 = M-Toluic-acid-3D-balls.png
| ImageSizeR1 = 125
| ImageAltR1 = Ball-and-stick model of the m-toluic acid molecule
| Reference = [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7418&loc=ec_rcs M-TOLUIC ACID - Compound Summary], PubChem.
| PIN = 3-Methylbenzoic acid
| OtherNames = meta-Toluic acid
m-Methylbenzoic acid
meta-Methylbenzoic acid
|Section1={{Chembox Identifiers
| SMILES = CC1=CC=CC(=C1)C(=O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = GPSDUZXPYCFOSQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 99-04-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1UA7K8EEXT
| RTECS =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 10589
| PubChem = 7418
| EINECS = 247-107-0
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C07211
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7140
}}
|Section2={{Chembox Properties
| Formula = C8H8O2
| MolarMass = 136.15 g/mol
| Appearance =
| Density = 1.05 g/cm3, solid
| Solubility =
| MeltingPtC = 111 to 113
| MeltingPt_notes =
| BoilingPtC = 263
| pKa = 4.27 (in water){{cite web |url=http://www.zirchrom.com/organic.htm |accessdate=11 April 2010 |title=Dissociation Constants Of Organic Acids And Bases}}
| Viscosity =
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/TO/m-toluic_acid.html External MSDS]
| MainHazards =
| FlashPt =
}}
|Section8={{Chembox Related
| OtherFunction_label = carboxylic acids
| OtherFunction =
}}
}}
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.{{cite journal | title = An interesting and successful organic experiment (CEC) | pages = 631 | journal = J. Chem. Educ. | author = Wang, Benjamin J-S. | year = 1974 | volume = 51 | issue = 10 | doi = 10.1021/ed051p631.2}}{{cite book | title = Introduction to organic laboratory techniques | author = Donald L. Pavia | isbn = 978-0-534-40833-6 | publisher = Cengage Learning | year = 2004 | pages = 370–376 | url = https://books.google.com/books?id=ega5c11VHvkC&pg=PA370 | format = Google Books excerpt}}