alpha-Bromo-p-toluenesulphonyl chloride Chemical Properties

Melting point:

71-75 °C(lit.)

Boiling point:

160-170 °C

Density 

1.6944 (estimate)

storage temp. 

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

form 

Crystalline Powder

color 

Off-white to light yellow

Sensitive 

Moisture Sensitive

BRN 

2364328

CAS DataBase Reference

66176-39-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

MSDS

• Language:English Provider:alpha-Bromo-p-toluenesulphonyl chloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

alpha-Bromo-p-toluenesulphonyl chloride Usage And Synthesis

Chemical Properties

off-white to light yellow crystalline powder

Uses

4-(Bromomethyl)benzenesulfonyl chloride may be used to synthesize:

• 4-bromomethyl-N-(6-methoxy-quinolin-8-yl)-benzenesulfonamide
• benzene-sulfonamide derivatives, which are potent Chemokine Receptor Type 4 (CXCR4) inhibitors
• imidazole derivatives having antifungal activity

Synthesis

General procedure for the synthesis of 4-bromomethylbenzenesulfonyl chloride from p-toluenesulfonyl chloride: to a stirred solution of p-toluenesulfonyl chloride (20 g, 104.9 mmol) in carbon tetrachloride (500 mL) was added sequentially N-bromosuccinimide (20.6 g, 115.7 mmol) and benzoyl peroxide (2.54 g, 10.84 mmol) at room temperature. The reaction mixture was refluxed for 10 hours and then filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to give a yellow oil. The oily substance was recrystallized using hexane as eluent to give 4-bromomethylbenzenesulfonyl chloride (20.6 g, 65% yield) as a final white solid.

References

[1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 5, p. 1487 - 1493
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4232
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2437 - 2451
[5] Patent: US5318980, 1994, A

alpha-Bromo-p-toluenesulphonyl chloride(66176-39-4)Related Product Information

• Benzenesulfonyl chloride
• Mesitylene-2-sulfonyl chloride
• alpha-Bromo-p-toluenesulphonyl chloride
• alpha-Toluenesulfonyl chloride