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Revision as of 18:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 448270420 of page 4-Nitrobenzoic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 19:38, 31 January 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 edits recategorized from Nitrobenzenes to Nitrobenzene derivatives 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 447855620 | verifiedrevid = 477223100
|IUPACName=4-nitrobenzoic acid
| ImageFile = 4-nitrobenzoic acid.svg | ImageFile = 4-Nitrobenzoic acid.svg
| ImageSize = 70px | ImageSize = 70px
|OtherNames=''p''-nitrobenzoic acid | PIN = 4-Nitrobenzoic acid
| OtherNames = ''p''-Nitrobenzoic acid
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5882 | ChemSpiderID = 5882
| InChI = 1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10) | InChI = 1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=62-23-7 | CASNo=62-23-7
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=6108
| UNII = G83NWR61OW
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem=6108
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 262350 | ChEBI = 262350
| SMILES = O=()c1ccc(C(=O)O)cc1 | SMILES = O=()c1ccc(C(=O)O)cc1
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>7</sub>H<sub>5</sub>NO<sub>4</sub> | Formula=C<sub>7</sub>H<sub>5</sub>NO<sub>4</sub>
| MolarMass= 167.1189 g/mol<ref name="pubchem">{{cite web |url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6108 |accessdate=11. April 2010 |title="4-nitrobenzoic acid - PubChem Public Chemical Database"}}</ref> | MolarMass= 167.1189 g/mol<ref name="pubchem">{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6108 |access-date=11 April 2010 |title=4-nitrobenzoic acid - PubChem Public Chemical Database}}</ref>
| Appearance=Light yellow crystalline powder<ref name="msds.chem.ox.ac.uk">{{cite web |url=http://msds.chem.ox.ac.uk/NI/p-nitrobenzoic_acid.html |title="Safety data for p-nitrobenzoic acid" |accessdate=11. April 2010}}</ref> | Appearance=Light yellow crystalline powder<ref name="msds.chem.ox.ac.uk">{{cite web |url=http://msds.chem.ox.ac.uk/NI/p-nitrobenzoic_acid.html |title=Safety data for p-nitrobenzoic acid |access-date=11 April 2010 |archive-date=27 May 2008 |archive-url=https://web.archive.org/web/20080527161937/http://msds.chem.ox.ac.uk/NI/p-nitrobenzoic_acid.html |url-status=dead }}</ref>
| Density= 1.58<ref name="msds.chem.ox.ac.uk"/> | Density= 1.58<ref name="msds.chem.ox.ac.uk"/>
| MeltingPtC = 237
⚫ | MeltingPt= 237 °C<ref name="msds.chem.ox.ac.uk"/>
| BoilingPt=Sublimes<ref name="msds.chem.ox.ac.uk"/> | MeltingPt_ref = <ref name="msds.chem.ox.ac.uk"/>
⚫ | BoilingPt=Sublimes<ref name="msds.chem.ox.ac.uk"/>
| Solubility=&lt;0.1 g/100 mL at 26 ºC <ref name="chemicalbook">{{cite web |url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4252540.htm |title="p-Nitrobenzoic acid" |accessdate=11. April 2010}}</ref> | Solubility=&lt;0.1 g/100 mL at 26 °C <ref name="chemicalbook">{{cite web |url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4252540.htm |title=p-Nitrobenzoic acid |access-date=11 April 2010| archive-url= https://web.archive.org/web/20100507102413/http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4252540.htm| archive-date= 7 May 2010 <!--DASHBot-->| url-status=live}}</ref>
| pKa= 3.41 (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>, 9.1 (in ])<ref name="bordwell">{{cite web |url=http://www.chem.wisc.edu/areas/reich/pkatable |title="Bordwell pKa Table (Acidity in DMSO)" |accessdate=11. April 2010}}</ref> | pKa= 3.41 (in water),<ref name="pkaValues">{{cite web |url=http://www.zirchrom.com/organic.htm |access-date=11 April 2010 |title=Dissociation Constants Of Organic Acids And Bases}}</ref> 9.1 (in ])<ref name="bordwell">{{cite web |url=http://www.chem.wisc.edu/areas/reich/pkatable |title=Bordwell pKa Table (Acidity in DMSO) |access-date=11 April 2010}}</ref>
| MagSus = -78.81·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
|Section8= {{Chembox Related |Section8={{Chembox Related
| OtherCpds= ]<br>]<br>]<br>], ], ] | OtherCompounds = ]<br>]<br>]<br>], ], ]
}} }}
}} }}

'''4-Nitrobenzoic acid''' is an ] with the ] C<sub>6</sub>H<sub>4</sub>(NO<sub>2</sub>)CO<sub>2</sub>H. It is a pale yellow solid. It is a precursor to 4-nitrobenzoyl chloride, the precursor to the anesthetic ] and ]. It is also a precursor to ].<ref>{{cite encyclopedia|author1=Takao Maki |author2=Kazuo Takeda|title=Benzoic Acid and Derivatives|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a03_555|isbn=3527306730}}.</ref>

==Production==
4-Nitrobenzoic acid is prepared by oxidation of ] using oxygen or dichromate as oxidants.<ref>{{cite journal|author1=O. Kamm |author2=A. O. Matthews|title=p-Nitrobenzoic Acid|journal=Org. Synth.|year=1922|volume=2|pages=53|doi=10.15227/orgsyn.002.0053}}</ref>

:]

Alternatively, it has been prepared by nitration of ] followed by oxidation of the alkyl substituent. This method proceeds with improved para/ortho selectivity owing to the steric protection of the ortho positions by the polymer backbone.

== Safety ==
This compound has a rat {{LD50}} of 1960&nbsp;mg/kg.<ref name="scienceLab">{{cite web |url=http://www.sciencelab.com/msds.php?msdsId=9926264 |title=Material Safety Data Sheet - P-nitrobenzoic acid MSDS |access-date=11 April 2010 |archive-url=https://web.archive.org/web/20110807203755/http://www.sciencelab.com/msds.php?msdsId=9926264 |archive-date=7 August 2011 |url-status=dead }}</ref>

== References ==
<references/>

{{DEFAULTSORT:Nitrobenzoic acid, 4-}}
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