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Revision as of 06:41, 8 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 09:37, 8 December 2024 edit undoAluminiumWithAnI (talk | contribs)Extended confirmed users2,263 edits filled in 1 bare url 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 459535846 | verifiedrevid = 459589749
|ImageFile=Benzyl-cyanide.png | ImageFile =Benzyl-cyanide.png
|ImageSize=100px | ImageSize =100px
|IUPACName=2-Phenylacetonitrile
| ImageAlt = Skeletal formula of benzyl cyanide
|OtherNames= phenylacetonitrile, Éø-tolunitrile
| ImageFile1 = Benzyl-cyanide-3D-balls.png
⚫ |Section1= {{Chembox Identifiers
| ImageSize1 = 160
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| ImageAlt1 = Ball-and-stick model of the benzyl cyanide molecule
| PIN = Phenylacetonitrile<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 16 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| OtherNames = Benzyl cyanide<ref name=iupac2013 /><br />2-Phenylacetonitrile<br />α-Tolunitrile<br />Benzylnitrile
⚫ |Section1={{Chembox Identifiers
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C16074 | KEGG = C16074
| InChI = 1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 | InChI = 1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
| InChIKey = SUSQOBVLVYHIEX-UHFFFAOYAJ | InChIKey = SUSQOBVLVYHIEX-UHFFFAOYAJ
| SMILES = N#CCc1ccccc1
| SMILES1 = c1ccc(cc1)CC#N
| StdInChI = 1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 | StdInChI = 1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 16: Line 21:
| StdInChIKey = SUSQOBVLVYHIEX-UHFFFAOYSA-N | StdInChIKey = SUSQOBVLVYHIEX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=140-29-4 | CASNo =140-29-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | ChEBI = 25979
| UNII = 23G40PRP93
⚫ | PubChem=8794
| ChEBI_Ref = {{ebicite|correct|EBI}}
| SMILES=C1=CC=C(C=C1)CC#N
⚫ | ChEBI = 25979
⚫ | PubChem =8794
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13839308 | ChemSpiderID = 13839308
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>8</sub>H<sub>7</sub>N | Formula =C<sub>8</sub>H<sub>7</sub>N
| MolarMass=117.15 g/mol | MolarMass =117.15 g/mol
| Appearance=Colorless oily liquid | Appearance =Colorless oily liquid
| Density=1.015 g/cm<sup>3</sup> | Density =1.015 g/cm<sup>3</sup>
| MeltingPt=-24 °C | MeltingPtC = -24
| MeltingPt_notes =
| BoilingPt=233-234 °C
| BoilingPtC = 233 to 234
| Solubility=
| BoilingPt_notes =
⚫ }}
| Solubility =
⚫ |Section3= {{Chembox Hazards
| MagSus = -76.87·10<sup>−6</sup> cm<sup>3</sup>/mol
| MainHazards=
⚫ }}
| FlashPt=
⚫ |Section3={{Chembox Hazards
| Autoignition=
| MainHazards =
⚫ }}
| FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''Benzyl cyanide''' (abbreviated '''BnCN''') is an ] with the ] C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CN. This colorless oily aromatic liquid is a precursor to several derivatives.<ref name=Ullmann>Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke “Nitriles” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a17_363}}</ref> '''Benzyl cyanide''' (abbreviated '''BnCN''') is an ] with the ] C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CN. This colorless oily aromatic liquid is an important ] to numerous compounds in ].<ref name=Ullmann>{{cite journal|last1=Pollak|first1=Peter|last2=Romeder|first2=Gérard|last3=Hagedorn|first3=Ferdinand|last4=Gelbke|first4=Heinz-Peter|title=Nitriles|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a17_363|isbn=3527306730}}</ref>
It is also an important ] in certain species.<ref>{{cite news|title=Toxin Protects Migratory Locusts from Cannibalism|date=4 May 2023|url=https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus|publisher=]|access-date=8 December 2024}}</ref>


==Preparation==
==Synthesis, reactions, and applications==
Benzyl cyanide can be produced via ] between ] and ]<ref>{{cite journal|last1=Adams|first1=Roger|last2=Thal|first2=A. F.|title=Benzyl cyanide|journal=Organic Syntheses|date=1922|volume=2|page=9|doi=10.15227/orgsyn.002.0009}}</ref> and by ] of ].<ref>{{cite journal|last1=Hiegel|first1=Gene|last2=Lewis|first2=Justin|last3=Bae|first3=Jason|title=Conversion of α-Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid|journal=Synthetic Communications|date=2004|volume=34|issue=19|pages=3449–3453|doi=10.1081/SCC-200030958|s2cid=52208189}}</ref>
Benzyl cyanide is produced by the reaction of ] with ].


Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.<ref>{{cite journal |doi=10.1021/ja053027x|title=Mild Palladium-Catalyzed Selective Monoarylation of Nitriles|year=2005|last1=Wu|first1=Lingyun|last2=Hartwig|first2=John F.|journal=Journal of the American Chemical Society|volume=127|issue=45|pages=15824–15832|pmid=16277525}}</ref>
The compound's most important reactions involve the "active ] group," which is readily functionalized following deprotonation.<ref>{{OrgSynth | collvol = 6 | collvolpages = 199 | year= 1988 | title = New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile | authors = Masumi Itoh, Daijiro Hagiwara, Takashi Kamiya | prep = cv6p0199}}</ref><ref>{{OrgSynth | collvol = 3 | collvolpages = 715 | year= 1955 | title = α-Phenylcinnamonitrile | authors = Stanley Wawzonek, Edwin M. Smolin | prep = cv3p0715}}</ref>


==Reactions==
BnCN it is an important intermediate for a variety of useful – and some dangerous - compounds. It is used in the production of ], ], and other ]. For this reason it is on the U.S.'s ]. It is also used to make ] and also pethidine and ketobemidone (if further substituted).
Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be ] to give ]<ref>{{cite journal|last1=Adams|first1=Roger|last2=Thal|first2=A. F.|title=Phenylacetic acid|journal=Organic Syntheses|date=1922|volume=2|page=59|doi=10.15227/orgsyn.002.0059}}</ref> or it can be used in the ] to yield phenylacetic acid ].<ref>{{cite journal|last1=Adams|first1=Roger|last2=Thal|first2=A. F.|title=Ethyl Phenylacetate|journal=Organic Syntheses|date=1922|volume=2|page=27|doi=10.15227/orgsyn.002.0027}}</ref> Hydrogenation gives ].<ref>{{cite journal |doi=10.15227/orgsyn.023.0071|title=β-Phenylethylamine|journal=Organic Syntheses|year=1943|volume=23|page=71|first1=John C. Jr.|last1=Robinson|first2=H. R.|last2=Snyder}}</ref>


The compound contains an "active ]". Bromination occurs gives PhCHBrCN.<ref>{{cite journal |first1=C. M.|last1=Robb|first2=E. M.|last2=Schultz|doi=10.15227/orgsyn.028.0055|title=Diphenylacetonitrile|journal=Organic Syntheses|year=1948|volume=28|page=55}}</ref> A variety of base-induced reactions result in the formation of new ]s.<ref>{{cite journal|last1=Makosza|first1=M.|last2=Jonczyk|first2=A|title=Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile|journal=Organic Syntheses|date=1976|volume=55|page=91|doi=10.15227/orgsyn.055.0091}}</ref><ref>{{cite journal|last1=Itoh|first1=Masumi|last2=Hagiwara|first2=Daijiro|last3=Kamiya|first3=Takashi|title=New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile|journal=Organic Syntheses|date=1988|volume=6|page=199|doi=10.15227/orgsyn.059.0095}}</ref><ref>{{cite journal|last1=Wawzonek|first1=Stanley|last2=Smolin|first2=Edwin M.|title=α-Phenylcinnamonitrile|journal=Organic Syntheses|date=1955|volume=3|page=715|doi=10.15227/orgsyn.029.0083}}</ref>
BnCN is the precursor to ] and related compounds. For example, BnCN reacts with 1,3-dihalopropane in the presence of a strong base to form the cyclobutane precursor to ]. One route to ] involves ] of the ] compound. The Clemmensen reduction is avoided if the synthesis starts with ] of BnCN followed by hydrolysis and reductive amination.

==Uses==
Benzyl cyanide is used as a solvent<ref>{{cite journal|last1=Bien|first1=Hans-Samuel|last2=Stawitz|first2=Josef|last3=Wunderlich|first3=Klaus|title=Anthraquinone Dyes and Intermediates|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|page=29|doi=10.1002/14356007.a02_355|isbn=3527306730}}</ref> and as a starting material in the synthesis of ]s (e.g. ]),<ref>{{cite journal|last1=Ackermann|first1=Peter|last2=Margot|first2=Paul|last3=Müller|first3=Franz|title=Fungicides, Agricultural|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a12_085|isbn=3527306730}}</ref> fragrances (]), ]s,<ref name=Ullmann /> and other ]. The partial hydrolysis of BnCN results in ].<ref>{{cite journal|title=PHENYLACETAMIDE|journal=Organic Syntheses|volume=32|year=1952|pages=92|issn=0078-6209|doi=10.15227/orgsyn.032.0092}}</ref>

===Pharmaceuticals===
Benzyl cyanide is a useful ] to numerous pharmaceuticals. Examples include:
<ref name=William>{{cite book|last1=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia|date=2008|publisher=Elsevier Science|location=Norwich, NY|isbn=9780815515265|pages=182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410|edition=3rd|url=https://books.google.com/books?id=bRX8MwEACAAJ&q=9780815515265}}</ref>
*]s (e.g. ])<ref name=William />
*Antidepressants: E.g. ] & ]
*]s (e.g. ] (para-fluoro),<ref name=William /><ref>{{cite journal|last1=Berkoff|first1=Charles E.|last2=Rivard|first2=Donald E.|last3=Kirkpatrick|first3=David|last4=Ives|first4=Jeffrey L.|title=The Reductive Decyanation of Nitriles by Alkali Fusion|journal=Synthetic Communications|date=1980|volume=10|issue=12|pages=939–945|doi=10.1080/00397918008061855}}</ref> ] & ].
*] (e.g. ], ], ], ], and ])<ref>{{cite journal|last1=Bub|first1=Oskar|last2=Friedrich|first2=Ludwig|title=Cough Remedies|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a08_013|isbn=3527306730}}</ref>
*] (e.g. ])<ref>{{cite journal|last1=Hropot|first1=Max|last2=Lang|first2=Hans-Jochen|title=Diuretics|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a09_029|isbn=3527306730}}</ref>
*]s (e.g. ] and ])<ref name=William /><ref name=Vogel>{{cite book|author1=Furniss, Brian |author2=Hannaford, Antony |author3=Smith, Peter |author4=Tatchell, Austin |name-list-style=amp |title=Vogel's Textbook of Practical Organic Chemistry 5th Ed.|year=1996|publisher=Longman Science & Technical|location=London|isbn=9780582462366|pages=1174–1179|url=https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd}}</ref> & ]
*] (e.g. ] and ])<ref name=William /><ref>{{cite journal|last1=Bungardt|first1=Edwin|last2=Mutschler|first2=Ernst|title=Spasmolytics|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a24_515|isbn=3527306730}}</ref>
*] (e.g. ])<ref name=William />
*] (e.g. ], ], and ])<ref name=William /> & ]

==Regulation==
Because benzyl cyanide is a useful ] to numerous ], many countries strictly regulate the compound.

===United States===
Benzyl cyanide is regulated in the United States as a ].

===China===
Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.<ref>{{cite web|url=http://www.gov.cn/zhengce/content/2021-06/07/content_5615890.htm|title=国务院办公厅关于同意将α-苯乙酰乙酸甲酯等6种物质列入易制毒化学品品种目录的函|publisher=The State Council - The People's Republic of China|language=zh-hans|date=7 June 2021|accessdate=11 October 2021}}</ref>


==Safety== ==Safety==
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.<ref name=Ullmann/> It is toxic and produces ] when burned. Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.<ref name=Ullmann/>
==See also==
*]


==References== ==References==
{{reflist}}
<references/>


==External links== ==External links==
* *


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