3-Cyanobenzene-1-sulfonyl chloride Chemical Properties

Melting point:

49-53 °C (lit.)

Boiling point:

148 °C

Density 

1.53±0.1 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

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

form 

powder to crystal

color 

White to Light yellow to Dark green

Sensitive 

Moistute Sensitive

BRN 

2832925

CAS DataBase Reference

56542-67-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-43-20/21/22

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 3

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Cyanobenzene-1-sulfonyl chloride Usage And Synthesis

Uses

A benzenesulfonamide derivative as potential kinase inhibitors.

Synthesis

General procedure for the synthesis of 3-cyanobenzenesulfonyl chloride from 3-aminobenzonitrile: 3-aminobenzonitrile (2.5 g, 21 mmol) was dissolved in concentrated hydrochloric acid. The mixture of hydrochloric acid (20 mL) and water (20 mL) was cooled to 0 °C and a solution of sodium nitrite (1.5 g, 22 mmol) in water (5 mL) was added slowly and dropwise. The reaction mixture was stirred at 0 °C for 10 min to ensure complete formation of the diazonium salt. In another flask, copper (I) chloride (0.2 g) was added to a solution of acetic acid (25 mL) pre-saturated with sulfur dioxide and stirred at 0°C for 10 minutes. This solution was slowly added dropwise to the above diazonium salt solution, kept at 0°C and stirred for 1 hour. After completion of the reaction, the mixture was poured into ice water and the product was extracted with tert-butyl methyl ether. The organic layers were combined and washed sequentially with water and brine. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% ethyl acetate in petroleum ether solution) to give pure 3-cyanobenzenesulfonyl chloride (1.9 g, 45% yield) as an off-white solid.1H NMR (300 MHz, CDCl3) δ 8.35 (t, J=1.5 Hz, 1H), 8.31-8.27 (m, 1H), and 8.06-8.02 (m, 1H), 7.82 (t, J=7.9Hz, 1H).

References

[1] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 11, p. 1833 - 1848
[2] Patent: EP2533783, 2015, B1. Location in patent: Paragraph 0335-0336
[3] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[4] Patent: US2002/128480, 2002, A1
[5] Patent: EP1258252, 2002, A1

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