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Sigma-Aldrich

Benzenesulfonamide

≥98%

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Synonym(s):
Phenylsulfonamide
Linear Formula:
C6H5SO2NH2
CAS Number:
Molecular Weight:
157.19
Beilstein/REAXYS Number:
1100566
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39093209
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98%

form

solid

mp

149-152 °C (lit.)

solubility

methanol: soluble 25 mg/mL

SMILES string

NS(=O)(=O)c1ccccc1

InChI

1S/C6H7NO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)

InChI key

KHBQMWCZKVMBLN-UHFFFAOYSA-N

Gene Information

human ... CA1(759)

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Application

Benzenesulfonamide was used to develop analytical method for simultaneous determination of benzotriazole, benzothiazole and benzenesulfonamide contaminants in environmental waters.

Biochem/physiol Actions

Benzenesulfonamide is an inhibitor of human carbonic anhydrase B. Benzenesulfonamide derivatives are effective in the treatment of proliferative diseases such as cancer. It is used in the synthesis of dyes, photochemicals and disinfectants.

Preparation Note

Benzenesulfonamide dissolves in methanol at a concentration of 25 mg/ml to form a clear, colourless solution.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Asha Chandran et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 92, 84-90 (2012-03-27)
The FT-IR and FT-Raman spectra of (E)-N-carbamimidoyl-4-((4-methoxybenzylidene)amino)benzenesulfonamide were recorded and analyzed. Geometry and harmonic vibrational wavenumbers were calculated theoretically using Gaussian 03 set of quantum chemistry codes. Calculations were performed at the Hartree-Fock (HF) and density functional theory (DFT) levels
Theres Ramenda et al.
Amino acids, 44(4), 1167-1180 (2013-01-12)
Cu(I)-mediated [3+2]cycloaddition between azides and alkynes has evolved into a valuable bioconjugation tool in radiopharmaceutical chemistry. We have developed a simple, convenient and reliable radiosynthesis of 4-[18F]fluoro-N-methyl-N-(propyl-2-yn-1-yl)benzenesulfonamide ([18F]F-SA) as a novel aromatic sulfonamide-based click chemistry building block. [18F]F-SA could be
Yousuke Takaoka et al.
Chemical communications (Cambridge, England), 49(27), 2801-2803 (2013-02-27)
Here we describe how a (19)F-probe incorporated into an endogenous protein by a chemical biology method revealed protein dynamics. By explicit determination of ligand-bound and unbound structures with X-ray crystallography, the quantitative comparison of the protein's dynamics in live cells
Nitrogen-15 nuclear magnetic resonance study of benzenesulfonamide and cyanate binding to carbonic anhydrase.
K Kanamori et al.
Biochemistry, 22(11), 2658-2664 (1983-05-24)
Genliang Lu et al.
Journal of medicinal chemistry, 56(2), 510-520 (2012-12-14)
Carbonic anhydrase IX (CA-IX) is upregulated in cancer in response to the hypoxic tumor microenvironment, making it an attractive molecular target for the detection of hypoxic solid tumors. A series of small molecule benzenesulfonamide based CA-IX inhibitors containing novel tridentate

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