Benzyl cyanide

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Benzyl cyanide
Benzyl-cyanide.png
Identifiers
CAS number 140-29-4 YesY
PubChem 8794
ChemSpider 13839308 YesY
KEGG C16074 YesY
ChEBI CHEBI:25979 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C8H7N
Molar mass 117.15 g/mol
Appearance Colorless oily liquid
Density 1.015 g/cm3
Melting point −24 °C (−11 °F; 249 K)
Boiling point 233 to 234 °C (451 to 453 °F; 506 to 507 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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

The compound's most important reactions involve the "active methylene unit" 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[edit]

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[edit]

  1. ^ 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
  2. ^ Masumi Itoh, Daijiro Hagiwara, Takashi Kamiya (1988), "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile", Org. Synth. ; Coll. Vol. 6: 199 
  3. ^ Stanley Wawzonek, Edwin M. Smolin (1955), "α-Phenylcinnamonitrile", Org. Synth. ; Coll. Vol. 3: 715 

External links[edit]