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545716

Sigma-Aldrich

3-Bromobenzenesulfonyl chloride

96%

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About This Item

Linear Formula:
BrC6H4SO2Cl
CAS Number:
Molecular Weight:
255.52
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

refractive index

n20/D 1.593 (lit.)

bp

90-91 °C/0.5 mmHg (lit.)

mp

30-33 °C

density

1.773 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

ClS(=O)(=O)c1cccc(Br)c1

InChI

1S/C6H4BrClO2S/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H

InChI key

PJGOLCXVWIYXRQ-UHFFFAOYSA-N

General description

3-Bromobenzenesulfonyl chloride is an aryl sulfonyl chloride derivative. It participates in the synthesis of N-sulfonylanthranilic acid derivatives and potent P1′ benzenesulfonyl azacyclic urea human immunodeficiency virus (HIV) protease inhibitors.

Application

3-Bromobenzenesulfonyl chloride may be used in the preparation of:
  • 2-(3-bromophenyl)-5-n-butylfuran
  • 2-(3-bromophenyl)-3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran
  • 3-bromo-4-(3-bromophenyl)thiophene
  • 2,5-bis(3-bromophenyl)-1-methylpyrrole

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Peggy P Huang et al.
Bioorganic & medicinal chemistry letters, 14(15), 4075-4078 (2004-07-01)
A series of novel azacyclic urea HIV protease inhibitors bearing a benzenesulfonamide group at P1' were synthesized utilizing a parallel synthesis method. Structural studies of early analogs bound in the enzyme active site were used to design more potent inhibitors.
Pd?Catalysed Direct Arylation of Heteroaromatics Using (Poly) halobenzenesulfonyl Chlorides as Coupling Partners: One Step Access to (Poly) halo?Substituted Bi (hetero) aryls.
Skhiri A, et al.
European Journal of Organic Chemistry, 2015(20), 4428-4436 (2015)
Zheng Yin et al.
Journal of medicinal chemistry, 52(24), 7934-7937 (2009-12-18)
A novel class of compounds containing N-sulfonylanthranilic acid was found to specifically inhibit dengue viral polymerase. The structural requirements for inhibition and a preliminary structure-activity relationship are described. A UV cross-linking experiment was used to map the allosteric binding site

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