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565849

Sigma-Aldrich

4-(Trifluoromethyl)benzenesulfonyl chloride

97%

Synonym(s):

α,α,α-Trifluoro-p-toluenesulfonyl chloride, 4-(Trifluoromethyl)benzene-1-sulfonyl chloride, [4-(Trifluoromethyl)phenyl]sulfonyl chloride, [p-(Trifluoromethyl)phenyl]sulfonyl chloride, p-Trifluoromethylbenzenesulfonyl chloride

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About This Item

Linear Formula:
CF3C6H4SO2Cl
CAS Number:
2991-42-6
Molecular Weight:
244.62
Beilstein:
2113604
MDL number:
MFCD00042422
UNSPSC Code:
12352100
PubChem Substance ID:
24880261
NACRES:
NA.22

Assay

97%

mp

30-34 °C (lit.)

SMILES string

FC(F)(F)c1ccc(cc1)S(Cl)(=O)=O

InChI

1S/C7H4ClF3O2S/c8-14(12,13)6-3-1-5(2-4-6)7(9,10)11/h1-4H

InChI key

OZDCZHDOIBUGAJ-UHFFFAOYSA-N

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Application

4-(Trifluoromethyl)benzenesulfonyl chloride may be used to synthesize β-arylated thiophenes and 2,5-diarylated pyrrolevia palladium catalyzed desulfitative arylation of thiophenes and pyrroles, respectively.
4-(Trifluoromethyl)benzenesulfonyl chloride and N-vinylpyrrolidinone in acetonitrile can undergo photo-irradiation with visible light in the presence of Ir(ppy)2(dtbbpy)PF6 ([4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis[2-(2-pyridinyl-N)phenyl-C]iridium(III)hexafluorophosphate) and disodium phosphate to give the corresponding E-vinyl sulfone.

Caution

Low Melting Solid

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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"Benzenesulfonyl chlorides: new reagents for access to alternative regioisomers in palladium-catalysed direct arylations of thiophenes"
Yuan K, et al.
Chemical Science, 5(1), 392-396 (2014)
"C-H Functionalization of Enamides: Synthesis of ?-Amidovinyl Sulfones via Visible-Light Photoredox Catalysis"
Jiang H, et al.
Advanced Synthesis & Catalysis, 355(4), 809-813 (2013)
Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners.
Jin R, et al.
Advanced Synthesis & Catalysis, 356(18), 3831-3841 (2014)

Articles

Aryl Sulfonyl Chloride Derivatives

Aryl sulfonyl chloride derivatives are frequently used in parallel synthesis to synthesize sulfonamides and sulfonate linkages.

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