Benzyl cyanide

Benzyl cyanide
Names
	IUPAC name 2-Phenylacetonitrile
	Other names phenylacetonitrile, Éø-tolunitrile
Identifiers
CAS Number	140-29-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:25979 ;
ChemSpider	13839308 ;
ECHA InfoCard	100.004.919
KEGG	C16074 ;
PubChem CID	8794;
CompTox Dashboard (EPA)	DTXSID2021492 ;
	InChI InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N ; InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Key: SUSQOBVLVYHIEX-UHFFFAOYAJ;
	SMILES C1=CC=C(C=C1)CC#N; c1ccc(cc1)CC#N;
Properties
Chemical formula	C8H7N
Molar mass	117.15 g/mol
Appearance	Colorless oily liquid
Density	1.015 g/cm3
Melting point	-24 °C
Boiling point	233-234 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C₆H₅CH₂CN. This colorless oily aromatic liquid is a precursor to several derivatives.^[1]

Synthesis, reactions, and applications

Benzyl cyanide is produced by the reaction of benzyl chloride with sodium cyanide.

The compound's most important reactions involve the "active methylene group," which is readily functionalized following deprotonation.^[2]^[3]

BnCN it is an important intermediate for a variety of useful – and some dangerous - compounds. It is used in the production of phenobarbital, methylphenidate, and other amphetamines. For this reason it is on the U.S.'s DEA List I of chemicals. It is also used to make methadone and also pethidine and ketobemidone (if further substituted).

BnCN is the precursor to sibutramine and related compounds. For example, BnCN reacts with 1,3-dihalopropane in the presence of a strong base to form the cyclobutane precursor to SEP-225289. One route to prolintane involves Clemmensen reduction of the pyrovalerone compound. The Clemmensen reduction is avoided if the synthesis starts with alkylation of BnCN followed by hydrolysis and reductive amination.

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.^[1] It is toxic and produces hydrogen cyanide when burned.

References

^ ^a ^b 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
^ "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses. 1988; Collected Volumes, vol. 6, p. 199.
^ "α-Phenylcinnamonitrile". Organic Syntheses. 1955; Collected Volumes, vol. 3, p. 715.

External links

EPA Chemical Profile for phenylacetonitrile

[Ullmann-1] 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

[2] "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses. 1988; Collected Volumes, vol. 6, p. 199.

[3] "α-Phenylcinnamonitrile". Organic Syntheses. 1955; Collected Volumes, vol. 3, p. 715.

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