Benzonitrile: Difference between revisions

|Watchedfields = changed

|verifiedrevid = 443416795

|ImageFileL1 = Benzonitrile structure.svg

|ImageNameL1 = Skeletal formula

|ImageFileR1 = Benzonitrile-3D-balls.png

|ImageNameR1 = Ball-and-stick model

|PIN = Benzonitrile <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

|SystematicName = Benzenecarbonitrile

|OtherNames=[[cyanide|cyano]][[benzene]] <br/> [[phenyl]] [[cyanide]]

|Section1={{Chembox Identifiers

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 9V9APP5H5S

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 27991

|SMILES = N#Cc1ccccc1

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = C09814

|InChI = 1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H

|PubChem = 7505

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 7224

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 15819

|InChIKey = JFDZBHWFFUWGJE-UHFFFAOYAY

|RTECS=DI2450000

|3DMet = B01115

|EINECS = 202-855-7

|Gmelin = 2653

|Beilstein = 506893

|UNNumber = 2224

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = JFDZBHWFFUWGJE-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo=100-47-0

}}

|Section2={{Chembox Properties

|Formula={{chem2|C6H5(CN)}}

|MolarMass=103.12 g/mol

|Density=1.0 g/ml

|MeltingPtC=-13

|BoilingPtC=188 to 191

|Solubility=&lt;0.5 g/100 ml (22 °C)

|Solvent=Water

|RefractIndex=1.5280

|MagSus = -65.19·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

|GHSPictograms = {{GHS07}}

|GHSSignalWord = Warning

|HPhrases = {{H-phrases|302|312}}

|PPhrases = {{P-phrases|264|270|280|301+312|302+352|312|322|330|363|501}}

|NFPA-H=3

|NFPA-F=2

|NFPA-R=0

|FlashPtC = 75

|AutoignitionPtC = 550

|ExploLimits=1.4&ndash;7.2%

}}

'''Benzonitrile''' is the [[chemical compound]] with the formula {{chem2|C6H5(CN)}}, abbreviated [[Phenyl|Ph]]CN. This [[aromatic]] [[organic compound]] is a colorless liquid with a sweet bitter [[almond]] odour. It is mainly used as a precursor to the resin [[benzoguanamine]].

==Production==

It is prepared by [[ammoxidation]] of [[toluene]], that is its reaction with [[ammonia]] and oxygen (or air) at {{convert|400|to|450|C|F}}.<ref>{{cite journal |title=Benzoic Acid and Derivatives |journal=Ullmann's Encyclopedia of Industrial Chemistry |first1=Takao |last1=Maki |first2=Kazuo |last2=Takeda |date=June 2000 |doi=10.1002/14356007.a03_555|isbn=3527306730 }}</ref>

:{{chem2|C6H5CH3}} + 3/2 {{chem2|O2}} + {{chem2|NH3}} → {{chem2|C6H5(CN)}} + {{chem2|3 H2O}}

In the laboratory it can be prepared by the dehydration of [[benzamide]] or [[benzaldehyde oxime]]<ref>{{cite journal | last1 = Loupy | first1 = André | last2 = Régnier | first2 = Serge | title = Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes | journal = Tetrahedron Letters | date = August 1999 | volume = 40 | issue = 34 | pages = 6221–6224 | issn = 0040-4039 | doi = 10.1016/S0040-4039(99)01159-4 | pmid = | url = }}</ref> or by the [[Rosenmund–von Braun reaction]] using [[cuprous cyanide]] or [[Sodium cyanide|NaCN]]/[[Dimethyl sulfoxide|DMSO]] and [[bromobenzene]].

:[[Image:Rosenmund-von Braun synthesis.svg|Rosenmund-von Braun synthesis]]

===Laboratory uses===

Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.<ref>{{OrgSynth |title=N-Phenylbenzamidine |first1=F. C. |last1=Cooper |first2=M. W. |last2=Partridge |collvol=4 |collvolpages=769 |year=1963 |prep=cv4p0769}}</ref> It is a precursor to [[Benzophenone imine| diphenylmethanimine]] via reaction with [[phenylmagnesium bromide]] followed by [[methanolysis]].<ref>{{OrgSynth |title=Diphenyl Ketimine |first1=P. L. |last1=Pickard |first2=T. L. |last2=Tolbert |collvol=5 |collvolpages=520 |year=1973 |prep=cv5p0520}}</ref>

Benzonitrile forms [[coordination complex]]es with transition metals that are both soluble in organic solvents and conveniently labile. One example is [[Bis(benzonitrile)palladium dichloride|{{chem2|PdCl2(PhCN)2}}]]. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.<ref>{{cite book |chapter=Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum |title=Reagents for Transition Metal Complex and Organometallic Syntheses |series=[[Inorganic Syntheses]] |publisher=John Wiley & Sons |first1=Gordon K. |last1=Anderson |first2=Minren |last2=Lin |volume=28 |pages=60–63 |date=1990 |doi=10.1002/9780470132593.ch13 |isbn=978-0-470-13259-3}}</ref>

Benzonitrile was reported by [[Hermann von Fehling|Hermann Fehling]] in 1844. He found the compound as a product from the thermal dehydration of [[ammonium benzoate]]. He deduced its structure from the already known analogue reaction of [[ammonium formate]] yielding [[hydrogen cyanide]] ([[Hydrogen_cyanide|formonitrile]]). He also coined the name benzonitrile which gave the name to all the group of [[nitrile]]s.<ref>{{cite journal |title=Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme |journal=[[Annalen der Chemie und Pharmacie]] |first=Hermann |last=Fehling |volume=49 |issue=1 |pages=91–97 |date=1844 |doi=10.1002/jlac.18440490106|url=https://zenodo.org/record/1426978 }}</ref>

In 2018, benzonitrile was reported to be detected in the [[interstellar medium]].<ref name="SC-20180112">{{cite journal |title=Detection of the aromatic molecule benzonitrile (c\sC6H5CN) in the interstellar medium |journal=[[Science (journal)|Science]] |first1=Brett A. |last1=McGuire |first2=Andrew M. |last2=Burkhardt |first3=Sergei |last3=Kalenskii |first4=Christopher N. |last4=Shingledecker |first5=Anthony J. |last5=Remijan |first6=Eric |last6=Herbst |first7=Michael C. |last7=McCarthy |display-authors=1 |volume=359 |issue=6372 |pages=202–205 |date=January 2018 |doi=10.1126/science.aao4890 |bibcode=2018Sci...359..202M |arxiv=1801.04228 |pmid=29326270|s2cid=206663501 }}</ref>

{{reflist}}

==External links==

{{Molecules detected in outer space}}

{{Authority control}}

[[Category:Aromatic solvents]]

[[Category:Phenyl compounds]]

[[Category:Benzonitriles]]

[[Category:Substances discovered in the 19th century]]