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Benzyl chloride

 

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Benzyl chloride



 
 
Benzyl chloride, or a-chlorotoluene, is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 consisting of a phenyl group substituted with a chloromethyl group.

yl chloride can be prepared by free radical chlorination
Free radical halogenation

In organic chemistry, free radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light....
 of toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 or the Blanc chloromethylation
Blanc chloromethylation

The Blanc chloromethylation is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride catalyzed by zinc chloride to form chloromethyl arenes....
 of benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
. Benzyl chloride is also easily prepared by mixing benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
 with a large molar excess of concentrated hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
.

yl chloride is used in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 for the introduction of the benzyl
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
 protecting group
Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction....
 for alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s (yielding the corresponding benzyl ether) and carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s (yielding the corresponding benzyl ester).






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Encyclopedia


Benzyl chloride, or a-chlorotoluene, is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 consisting of a phenyl group substituted with a chloromethyl group.

Preparation

Benzyl chloride can be prepared by free radical chlorination
Free radical halogenation

In organic chemistry, free radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of heat or UV light....
 of toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
 or the Blanc chloromethylation
Blanc chloromethylation

The Blanc chloromethylation is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride catalyzed by zinc chloride to form chloromethyl arenes....
 of benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
. Benzyl chloride is also easily prepared by mixing benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
 with a large molar excess of concentrated hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
.

Uses

Benzyl chloride is used in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 for the introduction of the benzyl
Benzyl

In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-....
 protecting group
Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction....
 for alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s (yielding the corresponding benzyl ether) and carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s (yielding the corresponding benzyl ester). It may be used in the synthesis of amphetamine-class drugs, and for this reason sales of benzyl chloride are monitored as a List II
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....
 drug precursor chemical by the Drug Enforcement Administration
Drug Enforcement Administration

The Drug Enforcement Administration is a United States Department of Justice law enforcement agency tasked with combating War on Drugs Not only is the DEA the lead agency for domestic enforcement of the drug policy of the United States , it also has sole responsibility for coordinating and pursuing U.S....
 in the United States of America.

Benzyl chloride reacts with water in a hydrolysis
Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
 reaction to form benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
 and hydrogen chloride
Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
. When the latter is dissolved in water, it forms hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. Since benzyl chloride is quite volatile
Volatility (chemistry)

Volatility in the context of chemistry, physics and thermodynamics is a measure of the tendency of a substance to vaporize. It has also been defined as a measure of how readily a substance vaporizes....
 at room temperature, it can easily reach the mucous membranes where the hydrolysis takes place with production of hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. This explains why benzyl chloride is a lachrymator
Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
 and has been used as a war gas
Chemical warfare

Chemical warfare involves using the poison of chemical substances as weapons to kill, injure, or incapacitate an Enemy .This type of warfare is distinct from the use of conventional weapons or nuclear weapons because the destructive effects of chemical weapons are not primarily due to their explosion force....
. It is also very irritating to the skin.

Benzyl chloride also reacts readily with metallic magnesium
Magnesium

Magnesium is a chemical element with the symbol Mg, atomic number 12, atomic weight 24.3050 and common oxidation number +2.Magnesium, an alkaline earth metal, is the ninth most abundance of the chemical elements in the universe by mass....
 to produce a Grignard Reagent, although the resulting benzyl magnesium chloride tends to dimer
Dimer

File:Carboxylic acid dimers.pngA dimer is a chemical or biological entity consisting of two identical subunits called monomers, which are held together by either intramolecular forces or weaker intermolecular forces....
ize due to the stability of the benzyl radical. This makes the use of benzyl Grignard reagents unfavorable.

A commonly used related compound is benzyl bromide
Benzyl bromide

Benzyl bromide, or a-bromotoluene, is an organic compound consisting of a benzene ring substituted with a bromomethyl group. It can be prepared by the bromination of toluene at room temperature in air, using manganese dioxide as a heterogeneous catalyst....
.