Benzyl cyanide
Encyclopedia
Benzyl cyanide is an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 C6H5CH2CN. This colorless oily aromatic liquid is a precursor to several derivatives.

Synthesis, reactions, and applications

Benzyl cyanide is produced by the reaction of benzyl chloride
Benzyl chloride
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block.-Preparation:...

 with sodium cyanide
Sodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...

.

The compound's most important reactions involve the "active methylene
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....

 group," which is readily functionalized following deprotonation.

BnCN it is an important intermediate for a variety of useful – and some dangerous - compounds. It is used in the production of phenobarbital
Phenobarbital
Phenobarbital or phenobarbitone is a barbiturate, first marketed as Luminal by Friedr. Bayer et comp. It is the most widely used anticonvulsant worldwide, and the oldest still commonly used. It also has sedative and hypnotic properties but, as with other barbiturates, has been superseded by the...

, methylphenidate
Methylphenidate
Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity...

, and other amphetamines. For this reason it is on the U.S.'s DEA List I of chemicals
DEA list of chemicals
The United States Drug Enforcement Administration maintains lists regarding not only the classification of illicit drugs . It also maintains List I of chemicals and List II of chemicals, which contain chemicals which are used to manufacture the controlled substances/illicit drugs...

. It is also used to make methadone
Methadone
Methadone is a synthetic opioid, used medically as an analgesic and a maintenance anti-addictive for use in patients with opioid dependency. It was developed in Germany in 1937...

 and also pethidine and ketobemidone (if further substituted).

BnCN is the precursor to sibutramine
Sibutramine
Sibutramine is an oral anorexiant. Until 2010 it was marketed and prescribed as an adjunct in the treatment of exogenous obesity along with diet and exercise...

 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
SEP-225289
SEP-225,289 is an antidepressant drug derived from the active enantiomer of sibutramine, which was being developed by Sepracor. It is a so-called triple reuptake inhibitor .-Further reading:Original Sibutramine patentsLiming Shao Patent...

. One route to prolintane
Prolintane
Prolintane is a stimulant of norepinephrine-dopamine reuptake inhibitors developed in the 1950s which is closely related in chemical structure to other drugs such as pyrovalerone and MDPV, and with a similar mechanism of action. It is a mild stimulant with a very good safety profile...

 involves Clemmensen reduction
Clemmensen reduction
Clemmensen reduction is a chemical reaction described as a reduction of ketones to alkanes using zinc amalgam and hydrochloric acid. This reaction is named after Erik Christian Clemmensen, a Danish chemist....

 of the pyrovalerone
Pyrovalerone
Pyrovalerone is a psychoactive drug with stimulant effects via acting as a norepinephrine-dopamine reuptake inhibitor , and is used for the clinical treatment of chronic fatigue or lethargy and as an anorectic or appetite suppressant for weight loss purposes...

 compound. The Clemmensen reduction is avoided if the synthesis starts with alkylation
Alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...

 of BnCN followed by hydrolysis and reductive amination.

Safety

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

External links

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