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Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation
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{{DISPLAYTITLE:''m''-Toluic acid}}
{{DISPLAYTITLE:''m''-Toluic acid}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 432418511
| Watchedfields = changed
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| Name = ''m''-Toluic acid
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| verifiedrevid = 447860534
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| ImageFileL1 = 3-toluic acid.svg
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| Name = ''m''-Toluic acid
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| ImageSizeL1 = 120px
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| ImageFileL1 = 3-toluic acid.svg
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| ImageNameL1 = Skeletal formula
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| ImageSizeL1 = 125
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| ImageFileR1 = M-Toluic-acid-3D-balls.png
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| ImageAltL1 = Skeletal formula of m-toluic acid
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| ImageSizeR1 = 120px
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| ImageFileR1 = M-Toluic-acid-3D-balls.png
| ImageNameR1 = Ball-and-stick model
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| ImageSizeR1 = 125
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| Reference = <ref>[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7418&loc=ec_rcs M-TOLUIC ACID - Compound Summary], [[PubChem]].</ref>
| ImageAltR1 = Ball-and-stick model of the m-toluic acid molecule
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| IUPACName = 3-Methylbenzoic acid
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| Reference = <ref>[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7418&loc=ec_rcs M-TOLUIC ACID - Compound Summary], [[PubChem]].</ref>
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| OtherNames = ''meta''-Toluic acid<br />''m''-Methylbenzoic acid<br />''beta''-Methylbenzoic acid
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| PIN = 3-Methylbenzoic acid
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| Section1 = {{Chembox Identifiers
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| OtherNames = ''meta''-Toluic acid<br />''m''-Methylbenzoic acid<br />''meta''-Methylbenzoic acid
| SMILES = O=C(O)c1ccccc1C
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|Section1={{Chembox Identifiers
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| CASNo_Ref = {{cascite}}
| 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
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 99-04-7
| CASNo = 99-04-7
| UNII_Ref = {{fdacite|correct|FDA}}
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| RTECS =
| PubChem = 7418
| UNII = 1UA7K8EEXT
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| 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
|Section2={{Chembox Properties
| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>2</sub>
| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>2</sub>
| MolarMass = 136.15 g/mol
| MolarMass = 136.15 g/mol
| Appearance =
| Appearance =
| Density = 1.05 g/cm³, solid
| Density = 1.05 g/cm<sup>3</sup>, solid
| Solubility =
| Solubility =
| MeltingPt = 111 - 113 °C
| MeltingPtC = 111 to 113
| MeltingPt_notes =
| BoilingPt = 263 °C
| BoilingPtC = 263
| pKa= 4.27 (in water)<ref name="pkaValues">{{cite web |url=http://www.zirchrom.com/organic.htm |accessdate=11. April 2010 |title="Dissociation Constants Of Organic Acids And Bases"}}</ref>
| pKa = 4.27 (in water)<ref name="pkaValues">{{cite web |url=http://www.zirchrom.com/organic.htm |accessdate=11 April 2010 |title=Dissociation Constants Of Organic Acids And Bases}}</ref>
| Viscosity =
| Viscosity =
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}}
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| Section7 = {{Chembox Hazards
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| ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/TO/m-toluic_acid.html External MSDS]
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| MainHazards =
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| FlashPt =
| RPhrases =
| SPhrases =
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}}
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| Section8 = {{Chembox Related
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| Function = [[carboxylic acid]]s
| OtherFunctn =
}}
}}
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|Section7={{Chembox Hazards
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| ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/TO/m-toluic_acid.html External MSDS]
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| MainHazards =
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| FlashPt =
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}}
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|Section8={{Chembox Related
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| OtherFunction_label = [[carboxylic acid]]s
| OtherFunction =
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}}
}}
}}


'''''m''-Toluic acid''', ([[IUPAC]]: '''3-methylbenzoic acid'''), is an [[aromatic]] [[carboxylic acid]], with formula (CH<sub>3</sub>)C<sub>6</sub>H<sub>4</sub>(COOH). It is an isomer of [[P-Toluic acid|''p''-toluic acid]] and [[O-Toluic acid|''o''-toluic acid]].
'''''m''-Toluic acid''', ([[IUPAC]]: '''3-methylbenzoic acid'''), is an [[aromatic]] [[carboxylic acid]], with formula (CH<sub>3</sub>)C<sub>6</sub>H<sub>4</sub>(COOH). It is an isomer of [[P-Toluic acid|''p''-toluic acid]] and [[O-Toluic acid|''o''-toluic acid]].


== Preparation ==
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It serves, among other purposes, as a precursor to [[DEET]] (''N'',''N''-diethyl-''m''-toluamide), the well-known [[insect repellent]]:<ref>{{cite journal | title = An interesting and successful organic experiment (CEC) | pages = 631 | journal = [[J. Chem. Ed.]] | author = Wang, Benjamin J-S. | year = 1974 | volume = 51 | issue = 10 | doi = 10.1021/ed051p631.2}}</ref><ref>{{cite book | title = Introduction to organic laboratory techniques | author = Donald L. Pavia | isbn = 9780534408336 | publisher = Cengage Learning | year = 2004 | pages = 370–376 | url = http://books.google.com/?id=ega5c11VHvkC&pg=PA370 | format = [[Google Books]] excerpt}}</ref>
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 ==
:[[Image:Preparation of DEET.png|500px]]
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It serves, among other purposes, as a precursor to [[DEET]] (''N'',''N''-diethyl-''m''-toluamide), the well-known [[insect repellent]].<ref>{{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}}</ref><ref>{{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}}</ref>


== References ==
== References ==
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{{DEFAULTSORT:Toluic acid, m-}}
{{DEFAULTSORT:Toluic acid, m-}}
[[Category:Benzoic acids]]
[[Category:Benzoic acids]]



{{aromatic-stub}}
{{aromatic-stub}}

[[ar:ميتا - حمض التولويك]]
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