776-04-5

Basic information

• Product Name: 2-(Trifluoromethyl)benzenesulfonyl chloride
• Synonyms: ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE-2-SULFONYL CHLORIDE;AKOS BBS-00006972;BUTTPARK 97\57-90;2-(TRIFLUOROMETHYL)BENZENESULFONYL CHLOR;2-(Trifluoromethyl)BenzenesulphonylChloride98%;2-(Trifluoromethyl)Benzenesulphonyl Chloride 98%;2-(Trifluoromethyl)benzenesulfonyl chloride ,97%;2-(Trifluoromethyl)benzenesulfonyl chloride,98%
• CAS NO: 776-04-5
• Molecular Formula: C₇H₄ClF₃O₂S
• Molecular Weight: 244.62
• EINECS: 1533716-785-6
• Product Categories: Fluorobenzene;API intermediates;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 776-04-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 133-135 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless to yellow liquid
• Density: 1.585 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00076mmHg at 25°C
• Refractive Index: n20/D 1.503(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2651854
• CAS DataBase Reference: 2-(Trifluoromethyl)benzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)benzenesulfonyl chloride(776-04-5)
• EPA Substance Registry System: 2-(Trifluoromethyl)benzenesulfonyl chloride(776-04-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 776-04-5(Hazardous Substances Data)

Usage

Description

2-(Trifluoromethyl)benzenesulfonyl chloride is an ortho-substituted benzenesulfonyl chloride, characterized by the presence of a trifluoromethyl group attached to the benzene ring. It is a clear colorless to yellow liquid with unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-(Trifluoromethyl)benzenesulfonyl chloride is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique trifluoromethyl group and benzenesulfonyl moiety contribute to the formation of novel drug molecules with potential therapeutic applications.
Used in Chemical Synthesis:
2-(Trifluoromethyl)benzenesulfonyl chloride is used as a reagent in organic synthesis, particularly for the preparation of various organic compounds. Its electrophilic nature allows it to participate in reactions such as nucleophilic substitution and addition, enabling the synthesis of a wide range of organic molecules.
Used in Material Science:
2-(Trifluoromethyl)benzenesulfonyl chloride is used as a building block in the development of new materials with specific properties. Its incorporation into polymers and other materials can lead to the creation of materials with improved characteristics, such as enhanced stability, reactivity, or selectivity.
Used in Agrochemical Industry:
2-(Trifluoromethyl)benzenesulfonyl chloride is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure can contribute to the development of more effective and targeted agrochemicals with reduced environmental impact.

InChI:InChI=1/C8H5F3N2S/c9-8(10,11)4-1-2-5-6(3-4)14-7(12)13-5/h1-3H,(H2,12,13)

Upstream product

• 13333-97-6 o-trifluoromethylbenzenethiol 

Downstream Products

• 111711-80-9 5-Ethoxy-1-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-2-one 
• 197959-54-9 5-methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenol 
• 503065-95-0 phenyl 3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 
• 887903-84-6 2-(2-trifluoromethyl-benzenesulfonyl)-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid ethyl ester 
• 848397-78-4 S-phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2-trifluoromethylbenzenesulfonyl)-β-D-thiomannopyranoside 

Relevant articles and documents

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.

A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides

2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.