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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 459589749 | verifiedrevid = 459589749
|ImageFile=Benzyl-cyanide.png | ImageFile =Benzyl-cyanide.png
|ImageSize=100px | ImageSize =100px
| ImageAlt = Skeletal formula of benzyl cyanide
|IUPACName=2-Phenylacetonitrile
| ImageFile1 = Benzyl-cyanide-3D-balls.png
|OtherNames= phenylacetonitrile, Éø-tolunitrile
| ImageSize1 = 160
⚫ |Section1= {{Chembox Identifiers
| ImageAlt1 = Ball-and-stick model of the benzyl cyanide molecule
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| 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
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 23G40PRP93
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 25979 | ChEBI = 25979
| PubChem=8794 | PubChem =8794
| SMILES=C1=CC=C(C=C1)CC#N
| 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|bibcode=2005JAChS.12715824W }}</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==
* *


{{Authority control}}
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Latest revision as of 17:10, 4 January 2025

Benzyl cyanide
Skeletal formula of benzyl cyanide
Ball-and-stick model of the benzyl cyanide molecule
Names
Preferred IUPAC name Phenylacetonitrile
Other names Benzyl cyanide
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.919 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N
  • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
SMILES
  • N#CCc1ccccc1
Properties
Chemical formula C8H7N
Molar mass 117.15 g/mol
Appearance Colorless oily liquid
Density 1.015 g/cm
Melting point −24 °C (−11 °F; 249 K)
Boiling point 233 to 234 °C (451 to 453 °F; 506 to 507 K)
Magnetic susceptibility (χ) -76.87·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain species.

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid or it can be used in the Pinner reaction to yield phenylacetic acid esters. Hydrogenation gives β-phenethylamine.

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN. A variety of base-induced reactions result in the formation of new carbon-carbon bonds.

Uses

Benzyl cyanide is used as a solvent and as a starting material in the synthesis of fungicides (e.g. Fenapanil), fragrances (phenethyl alcohol), antibiotics, and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:

Regulation

Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound.

United States

Benzyl cyanide is regulated in the United States as a DEA List I chemical.

China

Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.

See also

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 16. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_363. ISBN 3527306730.
  3. "Toxin Protects Migratory Locusts from Cannibalism". Max Planck Society. 4 May 2023. Retrieved 8 December 2024.
  4. Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses. 2: 9. doi:10.15227/orgsyn.002.0009.
  5. Hiegel, Gene; Lewis, Justin; Bae, Jason (2004). "Conversion of α-Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid". Synthetic Communications. 34 (19): 3449–3453. doi:10.1081/SCC-200030958. S2CID 52208189.
  6. Wu, Lingyun; Hartwig, John F. (2005). "Mild Palladium-Catalyzed Selective Monoarylation of Nitriles". Journal of the American Chemical Society. 127 (45): 15824–15832. Bibcode:2005JAChS.12715824W. doi:10.1021/ja053027x. PMID 16277525.
  7. Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses. 2: 59. doi:10.15227/orgsyn.002.0059.
  8. Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses. 2: 27. doi:10.15227/orgsyn.002.0027.
  9. Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses. 23: 71. doi:10.15227/orgsyn.023.0071.
  10. Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.
  11. Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91. doi:10.15227/orgsyn.055.0091.
  12. Itoh, Masumi; Hagiwara, Daijiro; Kamiya, Takashi (1988). "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses. 6: 199. doi:10.15227/orgsyn.059.0095.
  13. Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses. 3: 715. doi:10.15227/orgsyn.029.0083.
  14. Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry: 29. doi:10.1002/14356007.a02_355. ISBN 3527306730.
  15. Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN 3527306730.
  16. "PHENYLACETAMIDE". Organic Syntheses. 32: 92. 1952. doi:10.15227/orgsyn.032.0092. ISSN 0078-6209.
  17. ^ William Andrew Publishing (2008). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Norwich, NY: Elsevier Science. pp. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. ISBN 9780815515265.
  18. Berkoff, Charles E.; Rivard, Donald E.; Kirkpatrick, David; Ives, Jeffrey L. (1980). "The Reductive Decyanation of Nitriles by Alkali Fusion". Synthetic Communications. 10 (12): 939–945. doi:10.1080/00397918008061855.
  19. Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_013. ISBN 3527306730.
  20. Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_029. ISBN 3527306730.
  21. Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 1174–1179. ISBN 9780582462366.
  22. Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_515. ISBN 3527306730.
  23. "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" (in Simplified Chinese). The State Council - The People's Republic of China. 7 June 2021. Retrieved 11 October 2021.

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