4-Bromobenzyl chloride Chemical Properties

Melting point:

36-40 °C

Boiling point:

136-139 °C (27 mmHg)

Density 

1.3431 (rough estimate)

refractive index 

1.5750 (estimate)

Flash point:

106-107°C/10mm

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Powder and Granules

color 

White

Water Solubility 

Insoluble in water.

Merck 

14,1410

BRN 

6123220

InChI

InChI=1S/C7H6BrCl/c8-7-3-1-6(5-9)2-4-7/h1-4H,5H2

InChIKey

BSIIGUGKOPPTPZ-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(CCl)C=C1

CAS DataBase Reference

589-17-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-4-(chloromethyl)-(589-17-3)

Safety Information

Hazard Codes 

C

Risk Statements 

36/37-34

Safety Statements 

45-36/37/39-25-26

RIDADR 

3261

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymator

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromobenzyl chloride Usage And Synthesis

Chemical Properties

light yellow crystal powder to light yellow liqui

Uses

4-Bromobenzyl chloride is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Synthesis

General procedure for the synthesis of 4-bromobenzyl chloride from 4-bromobenzyl alcohol: 4-bromobenzyl alcohol (0.6 g, 0.6 mmol) and dichloromethane (5 mL) were added to a round bottom flask. After stirring for 10 min, oxalyl chloride or oxalyl bromide (0.6 mmol) was slowly added. The reaction mixture was magnetically stirred at room temperature. After the gas was released, 4-bromobenzyl alcohol (0.5 mmol) was added and the reaction mixture was heated to reflux. The progress of the reaction was monitored by TLC and after completion of the reaction, the mixture was cooled to room temperature and filtered. The solid on the funnel was washed with dichloromethane (3 x 10 mL), the filtrate was combined and concentrated under reduced pressure. The purity of the resulting 4-bromobenzyl chloride was confirmed by 1H NMR and 13C NMR spectral analysis.

Purification Methods

Crystallise the chloride from EtOH and distil it in a vacuum. [Beilstein 5 IV 832.] LACHRYMATORY.

References

[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[2] Organic Letters, 2013, vol. 15, # 1, p. 108 - 111
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4016 - 4024
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3434 - 3436
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064

4-Bromobenzyl chloride(589-17-3)Related Product Information

• Benzyl chloroformate
• Calcium chloride
• 1-Bromo-3-chloro-5,5-dimethylhydantoin
• Polyvinyl chloride
• Bromoxynil octanoate
• 4-Bromobenzoic acid
• Sulfuryl chloride
• Ferric chloride
• 4-Bromomethylbenzoic acid
• 2-Bromobenzonitrile
• 4'-Bromoacetophenone
• 4'-Bromopropiophenone
• 4-Bromobenzaldehyde
• 3-Chlorobenzyl chloride
• Choline chloride
• Bromobenzene
• 2-Bromofluorobenzene
• Benzene