2-METHOXYBENZENESULFONYL CHLORIDE Chemical Properties

Melting point:

50-54°C

Boiling point:

126-129 °C(Press: 0.3 Torr)

Density 

1.376

storage temp. 

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

Appearance

Light brown to brown Solid

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C7H7ClO3S/c1-11-6-4-2-3-5-7(6)12(8,9)10/h2-5H,1H3

InChIKey

GYOBZOBUOMDRRN-UHFFFAOYSA-N

SMILES

C1(S(Cl)(=O)=O)=CC=CC=C1OC

CAS DataBase Reference

10130-87-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

34-43

Safety Statements 

26-36/37/39-36/37

RIDADR 

3261

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2930909899

2-METHOXYBENZENESULFONYL CHLORIDE Usage And Synthesis

Uses

For synthesis and pharmacological evaluation of sulfonamide derivatives of thiazolidin-4-ones 5-Bromo-2-methoxybenzenesulfonyl chloride is used.

Synthesis

General procedure for the synthesis of 2-methoxybenzenesulfonyl chloride from 2-methoxybenzenethiol: To a solution of 2-methoxybenzenethiol (1 eq.) and isopropanol (CAS: 67-63-0) (2 eq.) in methylene chloride (0.15 M) was added batchwise N-bromosuccinimide (CAS: 128-08-5) or N-chlorosuccinimide (CAS: 128-09- 6) (4 or 3.5 equivalents), and the reaction was carried out at room temperature (when using NBS) or at 0 °C (when using NCS). The reaction mixture was stirred at room temperature until the starting material was undetectable by thin layer chromatography (TLC) (about 1 hour). Subsequently, the reaction mixture was diluted with cold saturated NaHCO3 solution and extracted with ethyl acetate (4 times). The organic extracts were combined, dried with Na2SO4 and concentrated in vacuum to give the crude product. Finally, pure 2-methoxybenzenesulfonyl chloride was purified by silica gel column chromatography or radial chromatography using a hexane/ethyl acetate/acetone solvent mixture as eluent to obtain pure 2-methoxybenzenesulfonyl chloride.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 23, p. 2244 - 2247
[2] Green Chemistry, 2017, vol. 19, # 9, p. 2286 - 2295

2-METHOXYBENZENESULFONYL CHLORIDE(10130-87-7)Related Product Information

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