4-BROMOBENZYLSULFONYL CHLORIDE Chemical Properties

Melting point:

117 °C

Boiling point:

116.5-121.5/

Density 

1.746±0.06 g/cm3(Predicted)

storage temp. 

-20°C, sealed storage, away from moisture

form 

powder

color 

White

CAS DataBase Reference

53531-69-4

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

22

RIDADR 

UN3261

Hazard Note 

Corrosive

HazardClass 

8

HS Code 

2904990090

4-BROMOBENZYLSULFONYL CHLORIDE Usage And Synthesis

Synthesis

General procedure for the synthesis of p-bromobenzyl sulfonyl chloride from 4-bromo-α-toluene thioacetic acid: N-chlorosuccinimide (NCS, 3.3 g, 24.6 mmol) was added batchwise to a solution of acetonitrile (30 mL) containing 2 M HCl (1.547 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 5 min. Subsequently, a solution of 4-bromophenylmethanesulfonyl chloride (1.5 g, 6.15 mmol) in acetonitrile (3 mL) was added dropwise to the mixture at the same temperature, with the dropwise addition time being controlled at 1 min. After continuing to stir the reaction mixture for 10 minutes, anhydrous sodium sulfate (about 5 g) was added and the solid was removed by filtration. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10/1) to afford p-bromobenzylsulfonyl chloride (1.2 g, 73% yield) as a white solid.1H NMR (300 MHz, CDCl3): δ = 7.62 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.4 Hz, 2H), 4.83 (s 2H).

References

[1] Patent: WO2018/132372, 2018, A1. Location in patent: Paragraph 01167
[2] Patent: US2014/163024, 2014, A1. Location in patent: Paragraph 0432
[3] Patent: US2014/163110, 2014, A1. Location in patent: Page/Page column 12
[4] Patent: WO2015/177325, 2015, A1. Location in patent: Page/Page column 52; 53

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