3-METHOXYBENZENESULFONYL CHLORIDE Chemical Properties

Boiling point:

158-159°C 20mm

Density 

1.460 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5560(lit.)

Flash point:

>230 °F

storage temp. 

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

form 

Liquid

color 

Clear pale yellow to pale brownish

Sensitive 

Moisture Sensitive

BRN 

2093871

CAS DataBase Reference

10130-74-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-36/37/39-45-39-37-36

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive/Moisture Sensitive

HazardClass 

8

PackingGroup 

II

HS Code 

29093090

MSDS

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

3-METHOXYBENZENESULFONYL CHLORIDE Usage And Synthesis

Chemical Properties

Clear pale yellow to pale brownish liquid

Uses

3-Methoxybenzenesulfonyl chloride may be used to synthesize 3-(4-phenylpiperazin-1yl) sulfonyls and N-(1-(4-methoxybenzyl)-3-cyclopropyl-1Hpyrazol-5-yl)-3-methoxybenzenesulfonamide.

Synthesis

In another flask, a mixed solution of 450 mL of glacial acetic acid with 45 mL of water was saturated with sulfur dioxide gas at 25°C (about 180 g of sulfur dioxide was required). To this saturated solution, 20.4 g (0.12 mol) of copper(II) chloride was added and sulfur dioxide gas was passed again to saturation. A pre-prepared and cooled diazonium salt solution was added slowly and dropwise to the above stirred mixture in the range of 20-26 °C. There was a release of gas during the reaction, followed by a slow increase of the reaction temperature to 38°C. When the temperature started to drop naturally, external heating was applied to keep the mixture stirred at 50°C for 15 minutes. Upon completion of the reaction, the mixture was cooled to room temperature and quenched by pouring into 2 kg of ice water. The oily product in the reaction mixture was extracted with ether (2 x 1000 mL). The ether layers were combined and washed sequentially with 1N NaOH solution (2×1000 mL), 1N HCl solution (2×1000 mL), and saturated brine (1×1000 mL), then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give 59.59 g of dark-colored oily crude product. The crude product was purified by silica gel column chromatography (silica gel dosage: 900 g) with dichloromethane/hexane (1:4, v/v) as eluent to give 43.52 g (43% yield) of 3-methoxybenzenesulfonyl chloride and 3.18 g of unidentified impurities. The products were analyzed by thin-layer chromatography (TLC) using silica gel plates with dichloromethane:hexane (1:1) as the unfolding agent, with an Rf value of 0.56 for the products and 0.41 for the impurities.

References

[1] Patent: US6342504, 2002, B1. Location in patent: Page column 124

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