Benzyl cyanide (abbreviated BnCN) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

chemical formula 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, such as pare ...

C₆H₅CH₂CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in

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

. It is also an important

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

in certain species.

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 organohalide, alkyl halide with a metal cyanide. A side product for this reaction is the formation of an isonitrile because the cyanide i ...

between

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

and

sodium cyanide Sodium cyanide is a compound with the formula Na C N and the structure . It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also expl ...

and by oxidative decarboxylation of

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

. 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 hydrolysi ...

to give

phenylacetic acid Phenylacetic acid (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. Endogenously ...

or it can be used in the Pinner reaction to yield phenylacetic acid

esters In chemistry, an ester is a chemical compound, compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds c ...

. Hydrogenation gives

β-phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

. 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 pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

s (e.g. Fenapanil), fragrances (

phenethyl alcohol Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula . It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of essential oils. It is slightly soluble in wate ...

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

s, and other

pharmaceuticals Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, 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 ...

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

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: *

Antiarrhythmic Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a class of drugs that are used to suppress abnormally fast rhythms (tachycardias), such as atrial fibrillation, supraventricular tachycardia and ventricular tachycardia. M ...

s (e.g.

disopyramide Disopyramide ( INN, trade names Norpace and Rythmodan) is an antiarrhythmic medication used in the treatment of ventricular tachycardia. It is a sodium channel blocker and is classified as a Class 1a anti-arrhythmic agent. Disopyramide has a neg ...

) *Antidepressants: E.g.

Milnacipran Milnacipran (trade names Ixel, Savella, Dalcipran, Toledomin) is a serotonin–norepinephrine reuptake inhibitor (SNRI) used in the clinical treatment of fibromyalgia, Major depressive disorder, and Neuropathic pain. In the US, it is solely appr ...

& Lomevactone *

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 ...

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

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 ana ...

(e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine) *

Diuretics A diuretic () is any substance that promotes diuresis, the increased production of urine. This includes forced diuresis. A diuretic tablet is sometimes colloquially called a water tablet. There are several categories of diuretics. All diuretics in ...

(e.g.

triamterene Triamterene (traded under names such as Dyrenium and Dytac) is a potassium-sparing diuretic often used in combination with thiazide diuretics for the treatment of high blood pressure or swelling. The combination with hydrochlorothiazide, is kno ...

) *

Hypnotic A hypnotic (from Ancient Greek, Greek ''Hypnos'', sleep), also known as a somnifacient or soporific, and commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to sleep induction, induce sleep and to trea ...

s (e.g. alonimid and

phenobarbital Phenobarbital, also known as phenobarbitone or phenobarb, sold under the brand name Luminal among others, is a medication of the barbiturate type. It is recommended by the World Health Organization (WHO) for the treatment of certain types of ...

) & Phenglutarimide * Spasmolytics (e.g. pentapiperide and drofenine) *

Stimulants Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognitio ...

(e.g.

methylphenidate Methylphenidate, sold under the brand names Ritalin ( ) and Concerta ( ) among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It may be taken Oral adm ...

), mazindol &

gamfexine Gamfexine (WIN-1,344) is a centrally acting stimulant drug, which was tested as an adjunct treatment for withdrawn patients with schizophrenia, but while effective for treating withdrawal it made psychotic symptoms worse. It was stated that gamf ...

. *

Opioids Opioids are a class of Drug, drugs that derive from, or mimic, natural substances found in the Papaver somniferum, opium poppy plant. Opioids work on opioid receptors in the brain and other organs to produce a variety of morphine-like effects, ...

(e.g. ethoheptazine,

pethidine Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Ot ...

, and phenoperidine) &

methadone Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid used medically to treat chronic pain and opioid use disorder. Prescribed for daily use, the medicine relieves cravings and opioid withdrawal sym ...

Regulation

Because benzyl cyanide is a useful precursor 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 Highly-toxic chemical substances Nitriles Benzyl compounds