3-Bromobenzyl bromide Chemical Properties

Melting point:

39-41 °C(lit.)

Boiling point:

130 °C12 mm Hg

Density 

1,56 g/cm³

refractive index 

1.6066 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Adhering Crystals or Crystalline Powder

color 

White

Water Solubility 

Insoluble in water.

BRN 

2078683

InChI

InChI=1S/C7H6Br2/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

InChIKey

ZPCJPJQUVRIILS-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC(CBr)=C1

CAS DataBase Reference

823-78-9(CAS DataBase Reference)

EPA Substance Registry System

Benzene, 1-bromo-3-(bromomethyl)- (823-78-9)

Safety Information

Hazard Codes 

C

Risk Statements 

34-37

Safety Statements 

26-36/37/39-45-25

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

19

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29036990

MSDS

• Language:English Provider:3-Bromobenzyl bromide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Bromobenzyl bromide Usage And Synthesis

Chemical Properties

White to yellow solid

Uses

3-Bromobenzyl bromide was used in the synthesis of, 1,7-di(3-bromobenzyl)cyclen and substituted 8-arylquinoline, phosphodiesterase 4 (PDE4) inhibitors.

Uses

3-Bromobenzyl bromide was used in the synthesis of:

• 1,7-di(3-bromobenzyl)cyclen
• substituted 8-arylquinoline, phosphodiesterase 4 (PDE4) inhibitors

General Description

3-Bromobenzyl bromide undergoes reduction with diethylzinc in the presence of Pd(PPh₃)₄ to yield corresponding hydrocarbon.

Synthesis

General procedure for the synthesis of 3-bromobenzyl bromide from 3-bromomethylbenzene: To a mixture of N-bromosuccinimide (NXS) and substrate (1 or 6) in acetonitrile (CH3CN), silicon tetrachloride (SiCl4) was slowly added at room temperature, and the reaction mixture was stirred continuously until thin-layer chromatography (TLC) monitoring showed complete disappearance of the feedstock. Subsequently, the reaction mixture was poured into water and extracted with dichloromethane (CH2Cl2). All organic phase extracts were combined and dried with anhydrous magnesium sulfate (MgSO4), followed by concentration under reduced pressure to remove the solvent. The residue was purified by recrystallization (petroleum ether-ether, 3:1) to give the pure products 2b-2g or 3b; or by silica gel column chromatography (hexane-ethyl acetate, 10:1 or 30:1) to give the pure products 2a, h, i, 3a-5 or 7-9.

References

[1] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[2] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
[3] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[4] Patent: US2009/12171, 2009, A1. Location in patent: Page/Page column 11
[5] Patent: WO2005/105736, 2005, A1. Location in patent: Page/Page column 28

3-Bromobenzyl bromide (823-78-9)Related Product Information

• Ethidium bromide
• 3-Fluorobenzyl chloride
• 3-Chlorobenzyl chloride
• Clidinium bromide
• 3-Bromophenol
• 3-Bromotoluene
• Diethylstilbestrol
• Sodium bromate
• BRETYLIUM TOSYLATE
• 3-Bromofluorobenzene
• 3-Bromobenzyl alcohol
• 3-Nitrobenzyl bromide
• (3-NITROPHENYL)ACETIC ACID METHYL ESTER
• 3-Bromoanisole
• 3-Nitroacetophenone
• 3-Nitrobenzaldehyde
• 1-Bromo-3-iodobenzene
• 3-Bromobenzonitrile
• Bromobenzyl Chloride