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542741

Sigma-Aldrich

5-Bromothiophene-2-sulfonamide

97%

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About This Item

Empirical Formula (Hill Notation):
C4H4BrNO2S2
CAS Number:
53595-65-6
Molecular Weight:
242.11
MDL number:
MFCD00067990
UNSPSC Code:
12352100
PubChem Substance ID:
24878630
NACRES:
NA.22

assay

97%

mp

138-142 °C (lit.)

SMILES string

NS(=O)(=O)c1ccc(Br)s1

InChI

1S/C4H4BrNO2S2/c5-3-1-2-4(9-3)10(6,7)8/h1-2H,(H2,6,7,8)

InChI key

WXJQQLDICAOBJB-UHFFFAOYSA-N

General description

5-Bromothiophene-2-sulfonamide can be synthesized by reacting 5-bromothiophene-2-sulfonyl fluoride with ammonium hydroxide in 2-methyltetrahydrofuran.

Application

5-Bromothiophene-2-sulfonamide may be used to synthesize:
  • 5-(phenylthio)thiophene-2-sulfonamide
  • 5-bromothiophene-2-sulfonyl acetamide
  • 5-arylthiophene-2-sulfonylacetamide derivatives

It may also be used in the preparation of the following 5-arylthiophene-2-sulfonamides:
  • 5-phenylthiophene-2-sulfonamide
  • 5-(3-cyno-5-(trifluoromethyl)phenyl)thiophene-2-sulfonamide
  • 5-(3,5-bis(trifluoromethyl)phenyl)thiophene-2-sulfonamide
  • 5′-chloro-2,2′-bithiophene-5-sulfonamide
  • 5′-methyl-2,2′-bithiophene-5-sulfonamide
  • 5-p-tolylthiophene-2-sulfonamide
  • 5-(4-methoxyphenyl)thiophene-2-sulfonamide
  • 5-(4-chlorophenyl)thiophene-2-sulfonamide
  • 5-(3,4-dichlorophenyl)thiophene-2-sulfonamide
  • 5-(3,5-dimethylphenyl)thiophene-2-sulfonamide
  • 5-(4-chloro-3-fluorophenyl)thiophene-2-sulfonamide

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1440747V
1442940V
1442940
1440747
01428DJ

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Mary M Mader et al.
Bioorganic & medicinal chemistry letters, 15(3), 617-620 (2005-01-25)
The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay.
Development of an Acyl Sulfonamide Anti-Proliferative Agent, LY573636? Na?.
Yates MH, et al.
Organic Process Research & Development, 13(2), 255-262 (2009)
A facile synthesis of new 5-aryl-thiophenes bearing sulfonamide moiety via Pd (0)-catalyzed Suzuki-Miyaura cross coupling reactions and 5-bromothiophene-2-acetamide: As potent urease inhibitor, antibacterial agent and hemolytically active compounds.
Noreen M, et al.
Journal of Saudi Chemical Society (2014)
I T Barnish et al.
Journal of medicinal chemistry, 24(8), 959-964 (1981-08-01)
A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the
Mnaza Noreen et al.
Molecules (Basel, Switzerland), 20(11), 19914-19928 (2015-11-12)
A variety of novel 5-aryl thiophenes 4a-g containing sulphonylacetamide (sulfacetamide) groups were synthesized in appreciable yields via Pd[0] Suzuki cross coupling reactions. The structures of these newly synthesized compounds were determined using spectral data and elemental analysis. Density functional theory

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