3-Chlorobenzyl bromide

3-Chlorobenzyl bromide Property

Melting point:

15 °C

Boiling point:

109-110 °C/12 mmHg (lit.)

Density 

1.565 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.588(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow

Specific Gravity

1.565

Water Solubility 

DECOMPOSES

Sensitive 

Lachrymatory

BRN 

636504

CAS DataBase Reference

766-80-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-(bromomethyl)-3-chloro-(766-80-3)

Safety

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

19

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

6.1

PackingGroup 

III

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

3-Chlorobenzyl bromide Chemical Properties,Usage,Production

Chemical Properties

Colorless liquid

Uses

3-Chlorobenzyl bromide was used in the synthesis of symmetrical and unsymmetrical benzyl thioethers. It was used as starting reagent during the synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole dihydrochloride.

General Description

3-Chlorobenzyl bromide reacts with aminoethanol and NaH to yield aminoethyl 3-chlorobenzyl ether.

Synthesis

General procedure for the synthesis of 3-chlorobenzyl bromide from 3-chlorotoluene: In a reaction flask fitted with a stirrer, reflux condenser, and thermometer, m-chlorotoluene (5.1 g, 40 mmol), sodium bromate (2.1 g, 14 mmol), sodium bromide (2.9 g, 28 mmol), and dichloromethane (25 mL) were added. A tail gas absorption device was installed and heated to reflux. AIBN (0.025 g) and BPO (0.025 g) were dissolved in 5 mL of dichloromethane and quickly added to the reaction flask. Subsequently, diluted concentrated sulfuric acid (2.1 g, 21 mmol, diluted with 2.5 mL of water) was added slowly and dropwise. Upon completion of the reaction, the progress of the reaction was monitored by gas chromatography. The mixture was cooled to room temperature, saturated sodium bisulfite solution (10 mL) was added and stirred until the solution faded from red to colorless. The aqueous phase was extracted twice with dichloromethane (10 mL x 2), the organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent was petroleum ether) to give 6.8 g of 3-chlorobenzyl bromide as a colorless liquid in 83% yield.

References

[1] Patent: CN107098791, 2017, A. Location in patent: Paragraph 0043-0045
[2] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
[3] Synthesis (Germany), 2018, vol. 50, # 24, p. 4933 - 4939
[4] Chinese Chemical Letters, 2011, vol. 22, # 4, p. 382 - 384
[5] Journal of the Chemical Society, 1932, p. 55,66