77745-03-0

Basic information

• Product Name: BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE
• Synonyms: BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE;BENZYL 2,2,2-TRIFLUOROETHYL SULPHIDE;2,2,2-TRIFLUOROETHYL SULFIDE;Benzyl 2,2,2-trifluoroethyl sulphide 97%;Benzyl2,2,2-trifluoroethylsulphide97%;2,2,2-Trifluoroethylbenzyl sulfide;2,2,2-trifluoroethylsulfanylmethylbenzene
• CAS NO: 77745-03-0
• Molecular Formula: C₉H₉F₃S
• Molecular Weight: 206.23
• Product Categories: Sulfides/Disulfides;Organic Building Blocks;Sulfur Compounds
• Mol File: 77745-03-0.mol

Chemical Properties

• Boiling Point: 45-46 °C20 mm Hg(lit.)
• Flash Point: 50 °F
• Appearance: /
• Density: 1.222 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.490(lit.)
• BRN: 4245572
• CAS DataBase Reference: BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE(77745-03-0)
• EPA Substance Registry System: BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE(77745-03-0)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 13
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 77745-03-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BENZYL 2,2,2-TRIFLUOROETHYL SULFIDE is used as a key intermediate in the preparation of trifluoroethanesulfonic acid, a strong acid with a wide range of applications in organic chemistry, including the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. Its trifluoromethyl group imparts unique reactivity and stability to the resulting products, making it a valuable building block in the development of new compounds with improved properties.

Synthesis Reference(s)

Canadian Journal of Chemistry, 65, p. 2385, 1987 DOI: 10.1139/v87-398

Upstream product

• 25236-64-0 2,2,2-trifluoroethyl methanesulfonate 
• 100-53-8 phenylmethanethiol 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 75-89-8 2,2,2-trifluoroethanol 
• 110-89-4 piperidine 
• 66950-71-8 2,2,2-trifluoroethyl fluorosulfate 
• 665-97-4 bis(2,2,2-trifluoroethyl) sulfate 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 

Downstream Products

• 1544-53-2 2,2,2-trifluoroethanethiol 
• 1648-99-3 2,2,2-Trifluoroethanesulfonyl chloride 
• 103624-50-6 {[(1-chloro-2,2,2-trifluoroethyl)sulfanyl]methyl}benzene 
• 103624-51-7 4-(1,1-dichloro2,2,2-trifluoro-ethylthio)methylbenzene 
• 130612-80-5 Benzyl 1,2,2,2-tetrafluoroethyl sulfide 
• 100-44-7 benzyl chloride 
• 192882-94-3 benzyl trifluorodithioacetate 
• 28203-59-0 (benzylsulfonyl)acetic acid 
• 111128-37-1 (1,1-Dichloro-2,2,2-trifluoro-ethanesulfonylmethyl)-benzene 

Relevant articles and documents

New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols

Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2F2) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55-90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.

Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes

Copper-catalyzed Si-H, B-H, P-H, S-H, and N-H insertion reactions of 2,2,2-trifluoro-1-diazoethane and 1-aryl 2,2,2-trifluorodiazoethanes generated a large number of new fluorine-containing chemical entities for medicinal chemists. With selected Si-H and

Synthesis of alkyl perfluoroalkanedithiocarboxylates and some aspects of their reactivity in cycloaddition reactions

A new method for the synthesis of the title compounds is proposed.The starting fluorinated compounds are commercially available trifluoroethanol and higher homologues, which were transformed in three steps into (2,2-dichloroperfluoroalkyl) alkylsulfides.The last step consisted in a substitution of chlorine by sulfur by treatment with zinc sulfide.The source of zinc sulfide is crucial and the possible role of catalytic impurities was investigated.These dithioesters are excellent dienophiles.Some cycloaddition reactions with 2,3-dimethylbuta-1,3-diene and 1-(trimethylsilyloxy)buta-1,3-diene are reported. - Keywords: perfluorinated dithioester; polyfluorinated sulfide; cycloaddition; tetrahydrothiopyran

Chemoselective reaction of a sulfonate ester with methoxide ions in preference to benzyl mercaptide anions

Trifluoroethyl benzyl sulfide was prepared (in 2-propanol) and subsequently chlorinated as a further test of substituent electronegativity based regiochemical predictions.The initial attempt to prepare that sulfide by reaction of 2,2,2-trifluoroethyl methanesulfonate and benzyl mercaptide anions (in methanol) furnished benzyl methyl sulfide.Mechanistic possibilities are discussed in detail and some synthetic consequences of this novel reaction are presented.

SYNTHESIS OF THREE PARTIALLY FLUORINATED ALKANESULFONIC ACIDS AS POTENTIAL FUEL-CELL ELECTROLYTES.

The simple and effective syntheses of CH//2FCH//2SO//3H, CF//3CH//2SO//3H, AND CHF//2CF//2CH//2SO//3H have been achieved with 18. 8%, 34. 1%, and 33. 7% overall yields. The low molecuar weight partially fluorinated alkanesulfonic acids containing alpha -methylene groups can be prepared from the p-toluenesulfonates of the corresponding alcohols, via a reaction with benzyl mercaptan, followed by an oxidative chlorination of the resulting sulfides, with subsequent hydrolysis of the sulfonyl chloride. The reaction of partially fluorinated alkyl halides with sodium sulfite (Strecker's method) proved to be inefficient (very low yields) and unreliable. The sulfonate salts formed are difficult to recover and purify.