Benzyl Bromide

Benzyl bromide From Wikipedia, the free encyclopedia Jump to: navigation, search Benzyl bromide[1]

IUPAC name

[show] Identifiers

CAS number

[100-39-0]

PubChem

7498

SMILES

[show] Properties

Molecular formula

C7H7Br

Molar mass

171.04 g/mol

Density

1.438 g/cm³ at 20 °C

Melting point Boiling point

-3.9 °C, 269 K, 25 °F 198-199 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Benzyl bromide, or α-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(IV) oxide as a heterogeneous catalyst. It is a colorless liquid that is decomposed slowly in water. Benzyl bromide is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids. Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used as a war gas.

[edit] Synthesis Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation:

N-Bromosuccinimide may also be used in place of elemental bromine.

Bromobenzene From Wikipedia, the free encyclopedia Jump to: navigation, search Bromobenzene

IUPAC name

[show]

Bromobenzene; Phenyl Bromide; Bromobenzol; Monobromobenzene

Other names

Identifiers CAS number

[108-86-1]

RTECS number

CY9000000

SMILES

[show] Properties

Molecular formula C6H5Br Molar mass

157.01 g mol−1

Appearance

Clear to slightly yellow liquid Pleasant aromatic odor

Density

1.495 g/cm³, liquid

Melting point

-30.8 °C (242.35 K)

Boiling point

156 °C (429.15 K) Insoluble (< 0.1 Solubility in water g/100ml at 25 C) Viscosity 1.124 cP at 20 °C Hazards Irritant (Xi), EU classification Environment (N) R-phrases R10, R38, R51/53 S-phrases (S2), S61 NFPA 704

2 2 0 Flash point 51 °C Related compounds Related Chlorobenzene Halogenobenzenes Iodobenzene Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Bromobenzenes are a group of halobenzenes formed in a substitution reaction between bromine and benzene with a hydrogen bromide by-product. The name strictly refers to monobromobenzene, a benzene with a single bromine; however it can be used to refer to a benzene containing any number of bromine molecules. Bromobenzene is a clear pale yellow liquid.

Uses Bromobenzene can be used to prepare the corresponding Grignard reagent, phenylmagnesium bromide. This can be used in a number of fashions, e.g. the reaction with carbon dioxide to prepare benzoic acid. Bromobenzene is used in the production of drugs.

[edit] Pharmacology It is a toxic substance and can cause liver and nervous system damage if inhaled, ingested or absorbed through the skin.