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Sigma-Aldrich

2-Fluorobenzenesulfonyl chloride

97%

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About This Item

Linear Formula:
FC6H4SO2Cl
CAS Number:
2905-21-7
Molecular Weight:
194.61
MDL number:
MFCD00042285
UNSPSC Code:
12352100
PubChem Substance ID:
24877907
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.537 (lit.)

bp

246-247 °C (lit.)

mp

27-30 °C (lit.)

density

1.47 g/mL at 25 °C (lit.)

SMILES string

Fc1ccccc1S(Cl)(=O)=O

InChI

1S/C6H4ClFO2S/c7-11(9,10)6-4-2-1-3-5(6)8/h1-4H

InChI key

ZSZKAQCISWFDCQ-UHFFFAOYSA-N

Related Categories

General description

2-Fluorobenzenesulfonyl chloride, also known as o-fluorobenzenesulfonyl chloride, is a flurinated arylsulfonyl chloride. It can be prepared from o-benzenedisulfonyl fluoride.

Application

2-Fluorobenzenesulfonyl chloride may be used in the preparation of the following furan derivatives:
  • 2-(2-fluorophenyl)benzofuran
  • 2-butyl-5-(2-fluorophenyl)furan
  • 2-(2-fluorophenyl)-3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran

It may also be used to prepare:
  • 2-fluorobenzenesulfonamide
  • methyl 2-{[(2-fluorophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylate
  • potassium fluorobenzene-2-sulfonate
  • 1-(2-bromobenzyl)-2-(2-fluorophenyl)pyrrole

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Regiocontroled Palladium?Catalysed Direct Arylation at Carbon C2 of Benzofurans using Benzenesulfonyl Chlorides as the Coupling Partners.
Loukotova L, et al.
ChemCatChem, 6(5), 1303-1309 (2014)
Water-Soluble Phosphines. 6.1 Tailor-Made Syntheses of Chiral Secondary and Tertiary Phosphines with Sulfonated Aromatic Substituents: Structural and Quantum Chemical Studies.
Bitterer F, et al.
Inorganic Chemistry, 35(14), 4103-4113 (1996)
Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: a structural basis for the reduction of albumin binding.
Sheppard GS, et al.
Journal of Medicinal Chemistry, 49(13), 3832-3849 (2006)
Potassium fluoride catalyzed fluorodesulfonylations of aryl sulfonyl fluorides.
Van der Puy M.
The Journal of Organic Chemistry, 53(18), 4398-4401 (1988)
Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans.
Beladhria A, et al.
Synthesis, 46(18), 2515-2523 (2014)
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