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, ...
C
6H
5CH
2CN. 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
Sodium cyanide is a poisonous compound with the formula Na C N. 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 exploits its hi ...
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 ...
of
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
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...
. 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 amin ...
.
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
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 pharmaceuticals. Examples include:
*
Antiarrhythmic
Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a group of pharmaceuticals that are used to suppress abnormally fast rhythms ( tachycardias), such as atrial fibrillation, supraventricular tachycardia and ventricular tac ...
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 therefore classified as a Class 1a anti-arrhythmic agent. Disopyramide has ...
)
*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. It is not approved for the clinical treatment of major depressive disorder in ...
&
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
Levocabastine (trade name Livostin or Livocab, depending on the region) is a selective second-generation H1 receptor antagonist which was discovered at Janssen Pharmaceutica in 1979. It is used for allergic conjunctivitis.
As well as acting as ...
(para-fluoro),
Pheniramine
Pheniramine (trade name Avil among others) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an ...
&
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
Isoaminile is an antitussive (cough suppressant) used under the trade-name Peracon.
The normal therapeutic dose is 40–80 mg of the cyclamate salt, with a maximum of five doses in a 24-hour period. In addition to its central antitussive ...
,
oxeladin,
butethamate,
pentapiperide, and
pentoxyverine
Pentoxyverine (rINN) or carbetapentane is an antitussive (cough suppressant) commonly used for cough associated with illnesses like common cold. It is sold over-the-counter in the United States as Solotuss,
or in combination with other medicatio ...
)
*
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 (trade name Dyrenium among others) 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 known as hydroch ...
)
*
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
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 ep ...
)
&
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
A muscle relaxant is a drug that affects skeletal muscle function and decreases the muscle tone. It may be used to alleviate symptoms such as muscle spasms, pain, and hyperreflexia. The term "muscle relaxant" is used to refer to two major therapeu ...
(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
Ethoheptazine (trade name Zactane) is an opioid analgesic from the phenazepane family. It was invented in the 1950s and is a ring expanded analogue of pethidine.
Ethoheptazine produces similar effects to other opioids, including analgesia, sedat ...
,
pethidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid analgesic, pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemis ...
, 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
Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid agonist used for chronic pain and also for opioid dependence. It is used to treat chronic pain, and it is also used to treat addiction to heroin ...
Regulation
Because benzyl cyanide is a useful
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
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.
[
]
See also
*Bromobenzyl cyanide
Bromobenzyl cyanide (BBC) is an obsolete lachrymatory agent introduced in World War I by the Allied Powers. When implemented in World War I, it revolutionized the use of tear agents due to their extreme potency. BBC is toxic like chlorine gas.AMO ...
References
External links
EPA Chemical Profile for phenylacetonitrile
{{Authority control
Nitriles
Benzyl compounds