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Benzyl bromide is an
The structure has been examined by electron diffraction.
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 formula . The molecule consists of a benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl group
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group ().
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a substituent, ...
s.
Synthesis and structure
Benzyl bromide can be synthesized by the bromination oftoluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water
Water is an inorganic compound with the c ...
under conditions suitable for a 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 UV light. The reaction is used for the industrial synthesis of chloroform ...
:
:
The structure has been examined by electron diffraction.
Applications
Benzyl bromide is used inorganic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
for the introduction of the benzyl groups when the less expensive 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 ...
is insufficiently reactive.
Benzylations are often achieved in the presence of catalytic amounts of sodium iodide
Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine. Under standard conditions, it is a white, water-soluble solid comprising a 1:1 mix of sodium cations (Na+) and iodide anions ...
, which generates the more reactive benzyl iodide in situ. In some cases, benzyl serves as protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis.
In man ...
for alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
s and carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
s.
Safety
Benzyl bromide is a stronglachrymator
Tear gas, also known as a lachrymatory agent or lachrymator (), sometimes colloquially known as "mace" after the Mace (spray), early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the ey ...
and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used in chemical warfare, both in combat and in training due to its irritating yet non-lethal nature.
See also
*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 ...
* Benzyl fluoride
* Benzyl iodide
* Xylyl bromide
Xylyl-bromide, also known as methylbenzyl bromide or T-stoff ('substance-T'), is any member or a mixture of organic chemical compounds with the molecular formula C6 H4(CH3)(CH2 Br). The mixture was formerly used as a tear gas and has an odor ...
References
{{Chemical agents Organobromides Benzyl compounds Lachrymatory agents