|Jmol-3D images||Image 1
|Molar mass||117.15 g/mol|
|Appearance||Colorless oily liquid|
|Melting point||-24 °C|
|Boiling point||233-234 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Synthesis, reactions, and applications
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.
- 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
- Masumi Itoh, Daijiro Hagiwara, Takashi Kamiya (1988), "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile", Org. Synth.; Coll. Vol. 6: 199
- Stanley Wawzonek, Edwin M. Smolin (1955), "α-Phenylcinnamonitrile", Org. Synth.; Coll. Vol. 3: 715