Benzyl cyanide (abbreviated BnCN) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

C₆H₅CH₂CN. This colorless oily aromatic liquid is an important

precursor Precursor or Precursors may refer to: *Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of unr ...

to numerous compounds in

organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

Preparation

Benzyl cyanide can be produced via

Kolbe nitrile synthesis The Kolbe nitrile synthesis is a method for the preparation of alkyl nitriles by reaction of the corresponding alkyl halide with a metal cyanide. A side product for this reaction is the formation of an isonitrile because the cyanide ion is an ambi ...

between

benzyl chloride Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared indust ...

and sodium cyanide and by

oxidative decarboxylation Oxidative decarboxylation is a decarboxylation reaction caused by oxidation. Most are accompanied by α- Ketoglutarate α- Decarboxylation caused by dehydrogenation of hydroxyl carboxylic acids such as carbonyl carboxylic acid, malic acid, isocitr ...

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

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

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be

hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

to give

phenylacetic acid Phenylacetic acid (PAA; conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogen ...

or it can be used in the

Pinner reaction The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt. The reaction is named after Adolf Pinner, who first described ...

to yield phenylacetic acid esters. Hydrogenation gives β-phenethylamine. The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN. A variety of base-induced reactions result in the formation of new carbon-carbon bonds.

Uses

Benzyl cyanide is used as a solvent and as a starting material in the synthesis of

fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

s (.e.g. Fenapanil), fragrances (

phenethyl alcohol Phenethyl alcohol, or 2-phenylethanol, is the organic compound that consists of a phenethyl group (C6H5CH2CH2) attached to OH. It is a colourless liquid that is slightly soluble in water (2 ml/100 ml H2O), but miscible with most organic solvents. ...

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

s, and other

pharmaceuticals A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and rel ...

. The partial hydrolysis of BnCN results in 2-phenylacetamide.

Pharmaceuticals

Benzyl cyanide is a useful

to numerous pharmaceuticals. Examples include: * Antiarrhythmics (e.g. disopyramide) *Antidepressants: E.g. Milnacipran &

Lomevactone Lomevactone (INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they a ...

Antihistamine Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provides re ...

s (e.g. levocabastine (para-fluoro), Pheniramine &

Azatadine Azatadine (Optimine) is a first-generation antihistamine and anticholinergic that was launched by Schering-Plough in 1973. It was patented in 1967. It has been succeeded by both loratadine and desloratadine. and marketing approvals have been ...

. *

Antitussives Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including a ...

(e.g. isoaminile,

oxeladin Oxeladin is a cough suppressant. It is a highly potent and effective drug used to treat all types of cough of various etiologies. It is not related to opium or its derivatives, so treatment with oxeladin is free of risk of dependence or addic ...

, butethamate, pentapiperide, and pentoxyverine) * Diuretics (e.g. triamterene) *

Hypnotic Hypnotic (from Greek ''Hypnos'', sleep), or soporific drugs, commonly known as sleeping pills, are a class of (and umbrella term for) psychoactive drugs whose primary function is to induce sleep (or surgical anesthesiaWhen used in anesthesia ...

s (e.g. alonimid and phenobarbital) &

Phenglutarimide Phenglutarimide (brand names Aturbal and Aturbane) is an anticholinergic used as an antiparkinsonian In the management of Parkinson's disease, due to the chronic nature of Parkinson's disease (PD), a broad-based program is needed that includes ...

* Spasmolytics (e.g. pentapiperide and

drofenine Drofenine is an antimuscarinic antispasmodic drug used for relaxing smooth muscle, thereby treating conditions, such as: dysmenorrhea, and pain in the gastrointestinal tract, biliary passages, and urogenital tract. Drofenine is assumed to work b ...

) *

Stimulants Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

(e.g.

methylphenidate Methylphenidate, sold under the brand names Ritalin and Concerta among others, is the most widely prescribed central nervous system (CNS) stimulant medication used to treat attention deficit hyperactivity disorder (ADHD) and, to a lesser extent, ...

) *

Opioids Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid use ...

(e.g. ethoheptazine, pethidine, and

phenoperidine Phenoperidine(Operidine or Lealgin), is an opioid analgesic which is structurally related to pethidine and is used clinically as a general anesthetic. Medical use Phenoperidine is an opioid pain killer -- narcotic analgesic. Pharmacology It i ...

) & methadone

Regulation

Because benzyl cyanide is a useful

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.

Safety

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

References

External links

EPA Chemical Profile for phenylacetonitrile
{{Authority control Nitriles Benzyl compounds