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Sigma-Aldrich

Benzenesulfonyl chloride

99%

Synonym(s):

Phenylsulfonyl chloride

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About This Item

Linear Formula:
C6H5SO2Cl
CAS Number:
98-09-9
Molecular Weight:
176.62
Beilstein/REAXYS Number:
606926
EC Number:
202-636-6
MDL number:
MFCD00007426
UNSPSC Code:
12352100
eCl@ss:
39092406
PubChem Substance ID:
24846802
NACRES:
NA.22

vapor pressure

0.04 mmHg ( 20 °C)

Quality Level

100

assay

99%

refractive index

n20/D 1.551 (lit.)

bp

251-252 °C (lit.)

mp

13-15 °C (lit.)

solubility

alcohol: soluble
cold water: insoluble
diethyl ether: soluble

density

1.384 g/mL at 25 °C (lit.)

SMILES string

ClS(=O)(=O)c1ccccc1

InChI

1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H

InChI key

CSKNSYBAZOQPLR-UHFFFAOYSA-N

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General description

Benzenesulfonyl chloride is prepared by reaction of benzene and chlorosulfonic acid or from the sodium salt of benzenesulfonic acid and PCl5 or POCl3. It reacts with Grignard reagent from N-unsubstituted indoles to form oxindoles or substituted indoles. Benzenesulfonyl chloride is the derivatization reagent for the determination of various amines in waste water and surface water at the sub-ppb level by gas chromatography-mass spectrometry.

Application

Benzenesulfonyl chloride may be used to develop fast, accurate and reproducible method for thiamine assay in different food products. It is useful reagent for preparing α-disulfones.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

260.6 °F

flash_point_c

127 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Benzenesulfonyl chloride
Adams R, et al.
Organic Syntheses, 1(84) (1921)
Synthesis, 490-490 (1993)
Unusual reactions of magnesium indolates with benzenesulfonyl chloride.
Wenkert E, et al.
The Journal of Organic Chemistry, 52(15), 3404-3409 (1987)
A Leone-Bay et al.
Journal of medicinal chemistry, 38(21), 4257-4262 (1995-10-13)
A series of benzoylated and phenylsulfonylated amino acids are novel, low molecular weight, self-assembling molecules. At low pH, these compounds form microspheres that dissolve readily under neutral conditions. In a given synthetic series, those molecules with low aqueous solubility formed
Ihor E Kopka et al.
Bioorganic & medicinal chemistry letters, 12(4), 637-640 (2002-02-15)
A series of substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl- and alpha-methyl-L-prolyl-phenylalanine derivatives was prepared as VLA-4/VCAM antagonists. The compounds showed excellent potency with a wide variety of neutral, polar, electron withdrawing or donating groups on the phenylalanine ring (IC50 approximately 1 nM). Heteroaryl ring
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