2991-42-6

Basic information

• Product Name: 4-(Trifluoromethyl)benzene-1-sulfonyl chloride
• Synonyms: P-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE;4-(TRIFLUOROMETHYL)BENZENESULPHONYL CHLORIDE;4-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE;4-(TRIFLUOROMETHYL)BENZENE-1-SULFONYL CHLORIDE;ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE-4-SULFONYL CHLORIDE;BUTTPARK 52\11-36;4-(Trifluoromethyl)benzenesulphonyl chloride 98%;4-(Trifluoromethyl)benzenesulphonylchloride98%
• CAS NO: 2991-42-6
• Molecular Formula: C₇H₄ClF₃O₂S
• Molecular Weight: 244.62
• EINECS: -0
• Product Categories: Fluorobenzene;Benzene series;Benzenesulfonyl chloride;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 2991-42-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 30-34 °C(lit.)
• Boiling Point: 76 °C
• Flash Point: 220 °F
• Appearance: White to pale yellow/Low Melting Solid
• Density: 1.532 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Sensitive: Moisture Sensitive
• BRN: 2113604
• CAS DataBase Reference: 4-(Trifluoromethyl)benzene-1-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethyl)benzene-1-sulfonyl chloride(2991-42-6)
• EPA Substance Registry System: 4-(Trifluoromethyl)benzene-1-sulfonyl chloride(2991-42-6)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 22-26-36/37/39-45-26 36/37/3945
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2991-42-6(Hazardous Substances Data)

Usage

Chemical Properties

White ro pale yellow low melting solid

Uses

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.

Upstream product

• 830-43-3 4-(trifluoromethyl)benzenesulfonamide 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 127-65-1 chloroamine-T 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 108789-37-3 benzyl(4-(trifluoromethyl)phenyl)sulfane 
• 455-14-1 4-trifluoromethylphenylamine 

Downstream Products

• 155134-48-8 (1R,2R)-N,N'-bis(4-trifluoromethylbenzenesulfonyl)-cyclohexane-1,2-diamine 
• 121148-20-7 1-tert-butyl 2-methyl (2S,4R)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 503065-94-9 phenyl 3-O-benzyl-2-O-(4-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 
• 105099-65-8 [4-(trifluoromethyl)benzenesulfonyl]isocyanate 

Relevant articles and documents

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Aromatic Chlorosulfonylation by Photoredox Catalysis

Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.