Benzyl cyanide

{{chembox

| Watchedfields = changed

| verifiedrevid = 459589749

| ImageFile =Benzyl-cyanide.png

| ImageSize =100px

| ImageAlt = Skeletal formula of benzyl cyanide

| ImageFile1 = Benzyl-cyanide-3D-balls.png

| ImageSize1 = 160

| ImageAlt1 = Ball-and-stick model of the benzyl cyanide molecule

| PIN = Phenylacetonitrile{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 16 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}

| OtherNames = Benzyl cyanide
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile

|Section1={{Chembox Identifiers

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

| KEGG = C16074

| InChI = 1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2

| InChIKey = SUSQOBVLVYHIEX-UHFFFAOYAJ

| SMILES = N#CCc1ccccc1

| StdInChI = 1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2

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

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

| StdInChIKey = SUSQOBVLVYHIEX-UHFFFAOYSA-N

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

| CASNo =140-29-4

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

| UNII = 23G40PRP93

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

| ChEBI = 25979

| PubChem =8794

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

| ChemSpiderID = 13839308

}}

|Section2={{Chembox Properties

| Formula =C₈H₇N

| MolarMass =117.15 g/mol

| Appearance =Colorless oily liquid

| Density =1.015 g/cm³

| MeltingPtC = -24

| MeltingPt_notes =

| BoilingPtC = 233 to 234

| BoilingPt_notes =

| Solubility =

| MagSus = −76.87·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| Hazards_ref = {{cite web |title=Phenylacetonitrile |url=https://pubchem.ncbi.nlm.nih.gov/compound/Phenylacetonitrile#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=4 May 2025 |language=en}}

| GHSPictograms = {{GHS skull and crossbones}}{{GHS exclamation mark}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|H301|H302|H311|H330}}

| PPhrases = {{P-phrases|P260|P262|P264|P270|P271|P280|P284|P301+P316|P301+P317|P302+P352|P304+P340|P316|P320|P321|P330|P361+P364|P403+P233|P405|P501}}

| NFPA-H = 3

| NFPA-F = 1

| NFPA-I = 0

| MainHazards = Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.

| FlashPt =

| AutoignitionPt =

}}

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.{{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}}

It is also an important pheromone in certain species.{{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=Max Planck Society|access-date=8 December 2024}}

Preparation

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

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

Reactions

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

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

Uses

Benzyl cyanide is used as a solvent{{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}} and as a starting material in the synthesis of fungicides (e.g. Fenapanil),{{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}} fragrances (phenethyl alcohol), antibiotics, and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.{{cite journal|title=PHENYLACETAMIDE|journal=Organic Syntheses|volume=32|year=1952|pages=92|issn=0078-6209|doi=10.15227/orgsyn.032.0092}}

=Pharmaceuticals=

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

{{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}}

Antiarrhythmics (e.g. disopyramide)
Antidepressants: E.g. Milnacipran & Lomevactone
Antihistamines (e.g. levocabastine (para-fluoro),{{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}} Pheniramine & Azatadine.
Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine){{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}}
Diuretics (e.g. triamterene){{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}}
Hypnotics (e.g. alonimid and phenobarbital){{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}} & Phenglutarimide
Spasmolytics (e.g. pentapiperide and drofenine){{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}}
Stimulants (e.g. methylphenidate), mazindol & gamfexine.
Opioids (e.g. ethoheptazine, pethidine, and phenoperidine) & methadone

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.{{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}}

Safety

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

References

External links

[http://yosemite.epa.gov/oswer/CeppoEHS.nsf/Profiles/140-29-4?OpenDocument EPA Chemical Profile for phenylacetonitrile]

Category:Highly-toxic chemical substances

Category:Nitriles

Category:Benzyl compounds