Benzyl chloride, or α-chlorotoluene, 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

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

C₆H₅CH₂Cl. This colorless liquid is a

reactive Reactive may refer to: *Generally, capable of having a reaction (disambiguation) *An adjective abbreviation denoting a bowling ball coverstock made of reactive resin *Reactivity (chemistry) *Reactive mind *Reactive programming See also *Reactanc ...

organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class ( alkanes with one or more hydrogens substituted by chlo ...

that is a widely used chemical building block.

Preparation

Benzyl chloride is prepared industrially by the

gas-phase Gas is one of the four fundamental states of matter (the others being solid, liquid, and plasma). A pure gas may be made up of individual atoms (e.g. a noble gas like neon), elemental molecules made from one type of atom (e.g. oxygen), or ...

photochemical Photochemistry is the branch of chemistry concerned with the chemical effects of light. Generally, this term is used to describe a chemical reaction caused by absorption of ultraviolet (wavelength from 100 to 400 nm), visible light (400–7 ...

reaction of

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...

with

chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...

: :C₆H₅CH₃ + Cl₂ → C₆H₅CH₂Cl + HCl In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the

free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...

process, involving the intermediacy of free chlorine atoms. Side products of the reaction include

benzal chloride Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis. Preparation and usage Benzal chloride is produced by the free radical chlorination o ...

and

benzotrichloride Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless (to yellowish), viscous, chlorinated hydr ...

. Other methods of production exist, such as the

Blanc chloromethylation The Blanc chloromethylation (also called the Blanc reaction) is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride to form chloromethyl arenes. The reaction is catalyzed by Lewis acids such as zinc chloride. The rea ...

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

. Benzyl chloride was first prepared from treatment of

benzyl alcohol Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid w ...

with

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

Uses and reactions

Industrially, benzyl chloride is the

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 u ...

to benzyl esters, which are used as

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

s, flavorants, and

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s. Phenylacetic acid, a precursor to pharmaceuticals, is produced from

benzyl cyanide Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. Preparation Benzyl cyanide can be produced via ...

, which in turn is generated by treatment of benzyl chloride with

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 ...

Quaternary ammonium salt In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations ...

s, used as surfactants, are readily formed by alkylation of

tertiary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

s with benzyl chloride. Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to give dibenzyl ether. In

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

, benzyl chloride is used to introduce the

benzyl In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group. Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substi ...

protecting group in reaction with alcohols, yielding the corresponding benzyl ether,

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

s, and benzyl ester.

Benzoic acid Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, wh ...

(C₆H₅COOH) can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO₄: :C₆H₅CH₂Cl + 2 KOH + 2 → C₆H₅COOK + KCl + H₂O Benzyl chloride may be used in the synthesis of amphetamine-class drugs, and for this reason, sales of benzyl chloride are monitored as a List II drug precursor chemical by the US

Drug Enforcement Administration The Drug Enforcement Administration (DEA; ) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within th ...

. Benzyl chloride also reacts readily with metallic

magnesium Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ta ...

to produce a

Grignard reagent A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...

. It is preferable over

benzyl bromide Benzyl bromide is an organic compound with the formula . The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl groups ...

for the preparation of this reagent, since the reaction of the bromide with magnesium tends to form the

Wurtz coupling In organic chemistry, the Wurtz reaction, named after Charles Adolphe Wurtz, is a coupling reaction whereby two alkyl halides are treated with sodium metal to form a higher alkane. : 2 R−X + 2 Na → R−R + 2 NaX The reaction is of little v ...

product 1,2-diphenylethane.

Safety

Benzyl chloride is an

alkylating agent 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 (or their equivalents). Alkylating agents are reagents for effectin ...

. Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride reacts with water in a

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

reaction to form

and

. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is a

lachrymator Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...

and has been used in

chemical warfare Chemical warfare (CW) involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from nuclear warfare, biological warfare and radiological warfare, which together make up CBRN, the military acronym ...

. It is also very irritating to the skin. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S.

Emergency Planning and Community Right-to-Know Act The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness. On October ...

(42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

References

External links

* *
CDC - NIOSH Pocket Guide for Chemical Hazards - Benzyl chloride
{{Authority control Organochlorides Lachrymatory agents IARC Group 2A carcinogens Benzyl compounds