933674-85-2

Basic information

• Product Name: 1-CHLORO-3-TRIFLUOROMETHANESULFONYL-BENZENE
• Synonyms: 3-(1,1,1-TRIFLUOROMETHANESULFONYL)CHLOROBENZENE;1-CHLORO-3-TRIFLUOROMETHANESULFONYL-BENZENE
• CAS NO: 933674-85-2
• Molecular Formula: C7H4ClF3O2S
• Molecular Weight: 244.62
• Mol File: 933674-85-2.mol

Chemical Properties

• Boiling Point: 286.2±40.0 °C(Predicted)
• Appearance: /
• Density: 1.533±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-CHLORO-3-TRIFLUOROMETHANESULFONYL-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-3-TRIFLUOROMETHANESULFONYL-BENZENE(933674-85-2)
• EPA Substance Registry System: 1-CHLORO-3-TRIFLUOROMETHANESULFONYL-BENZENE(933674-85-2)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 933674-85-2(Hazardous Substances Data)

Usage

Chemical structure

Chlorinated benzene derivative with three fluorine atoms and a sulfonyl group attached to the benzene ring

Functional groups

Chlorine, trifluoromethyl, sulfonyl

Applications

Used as a reagent in organic synthesis, particularly for the introduction of trifluoromethanesulfonyl (triflyl) groups to various organic molecules

Importance

Enhances nucleophilicity and stabilizes carbocations, making it valuable in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals

Versatility

Wide range of applications in various industries

Physical state

Likely a solid or liquid at room temperature (not specified in the material)

Reactivity

Reacts with nucleophiles to introduce triflyl groups into organic molecules

Safety

Potential hazards and safety precautions not specified in the material, but should be handled with care due to its reactivity and functional groups

Purity

Not specified in the material, but high purity is generally desired for use as a reagent in organic synthesis

Upstream product

• 2888-06-4 3-chlorophenylsulfonyl chloride 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 15946-37-9 sodium 3-chlorobenzenesulfinate 
• 2926-29-6 Langlois reagent 
• 1416277-01-4 (3-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate 

Relevant articles and documents

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

Practical and efficient synthesis of aryl trifluoromethyl sulfones from arylsulfonyl chlorides with Umemoto's reagent II

A practical and efficient method for the synthesis of aryl trifluoromethyl sulfones has been developed by a tandem reaction of arylsulfonyl chlorides with Umemoto's reagent II. The advantageous features of this method are simple operation, mild reaction conditions, wide scope of substrates, high yield of products, and easy scalability.

Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes

The direct synthesis of aryl triflones, that is, trifluoromethanesulfonyl arenes, was achieved through the trifluoromethanesulfonylation of benzynes. The trifluoromethanesulfonyl group, one of the fluorinated functional groups, is a highly electron-negative and mild lipophilic substituent. Aryl triflones have high potential in the synthesis of bioactive compounds and specialty materials. The treatment of 2-(trimethylsilyl)aryl trifluoromethanesulfonates with cesium fluoride in the presence of 15-crown-5 generated benzynes, which reacted with sodium trifluoromethanesulfinate followed by protonation with tBuOH under heating conditions, provided aryl triflones in moderated to good yields. Both symmetrical and unsymmetrical triflones were nicely accessed under the same reaction conditions. Interestingly, the trifluoromethanesulfonylation of unsymmetrical benzyne precursors proceeded smoothly to furnish corresponding aryl triflones in good yields with good to high regioselectivities. The balance of polarization of electric charge as well as steric hindrance of the benzyne intermediates are central factors to control the outcome of regioselectivity.

A method of manufacturing a benzene derivative (trifluoromethylsulfonyl)

PROBLEM TO BE SOLVED: To provide a method for producing a (trifluoromethylsulfonyl)benzene derivative which is useful as a medicine, an agricultural chemical, a functional material and a production intermediate thereof. SOLUTION: In this method, a (trifluoromethylsulfonyl)benzene derivative is produced by reacting diaryliodonium salt represented by general formula (1) with trifluoromethanesulfinic acid salt in the presence of a copper (I) salt. (In the formula, R1, R2, R3, R4, R5, R6, R7, R8, R9and R10each independently represents a hydrogen atom, a 1-6C alkyl group, a 1-6C haloalkyl group, a 1-6C alkoxy group, a 2-6C acyl group, (1-5C alkoxy)carbonyl group, a nitro group, a cyano group, a chlorine atom or a bromine atom). COPYRIGHT: (C)2013,JPOandINPIT