1648-99-3

Basic information

• Product Name: 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE
• Synonyms: TRESYL CHLORIDE;2,2,2-trifluoroethane-sulfonicacid,chloride;TIMTEC-BB SBB006545;2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE;2,2,2-TRIFLUOROETHANESULPHONYL CHLORIDE;(2,2,2-trifluoroethyl)sulphonyl chloride;2,2,2-Trifluoroethanesulphonylchloride,97+%;2,2,2-Trifluoroethanesulphonyl chloride 97%
• CAS NO: 1648-99-3
• Molecular Formula: C₂H₂ClF₃O₂S
• Molecular Weight: 182.55
• EINECS: 216-713-7
• Product Categories: Benzenesulfonyl chloride;organofluorine compounds
• Mol File: 1648-99-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 140-141 °C(lit.)
• Flash Point: 162 °F
• Appearance: Clear colorless/Liquid
• Density: 1.651 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.59mmHg at 25°C
• Refractive Index: n20/D 1.388(lit.)
• Storage Temp.: 2-8°C
• Sensitive: moisture sensitive
• BRN: 1860983
• CAS DataBase Reference: 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE(1648-99-3)
• EPA Substance Registry System: 2,2,2-TRIFLUOROETHANESULFONYL CHLORIDE(1648-99-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 3-10-19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1648-99-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

InChI:InChI=1/C2H2ClF3O2S/c3-9(7,8)1-2(4,5)6/h1H2

Upstream product

• 503-39-9 di-H-trifluoroethane-2-sulfonyl fluoride 
• 1544-53-2 2,2,2-trifluoroethanethiol 
• 77745-03-0 2,2,2-trifluoroethylthiomethylbenzene 
• 77745-01-8 2-Methyl-2-(2,2,2-trifluoro-ethylsulfanyl)-propane 
• 33802-55-0 2,2,2-Trifluoroethyl thiocyanate 

Downstream Products

• 117186-54-6 1,4-butanediol bis(2,2,2-trifluoroethanesulfonate) 
• 119481-36-6 2,2,2-Trifluoro-ethanesulfonic acid [3-(quinolin-2-ylmethoxy)-phenyl]-amide 
• 661461-84-3 N-(3-trifluoroethanesulfonyloxypropyl)anthraquinone-2-carboxamide 
• 503065-84-7 phenyl 3,4-di-O-benzyl-2-O-tresyl-1-thio-β-L-rhamnopyranoside 
• 593270-61-2 2,2,2-trifluoro-ethanesulfonic acid {3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-amide 
• 693824-44-1 C₂₇H₃₅F₆N₃O₂S 
• 353229-45-5 N-(3-(2-Methoxyphenoxy)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine 
• 353232-77-6 N-(4-(3-benzyloxyphenyl)-N-(2,2,2-trifluoroethanesulfonyl)pyrid-3-yl)methylamine 
• 777952-82-6 2,2,2-trifluoroethanesulfonic acid {1-[3-(3-dimethoxymethyl-1-methyl-1H-pyrazol-5-yl)-phenyl]-1-methylethyl}amide 
• 1025882-98-7 2,2,2-trifluoro-ethanesulfonic acid [1-(3-methoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-amide 

Relevant articles and documents

The first example of sulfinatodehalogenation of 2,2,2-trifluoroethyl halides: A novel method for trifluoroethylation of alkenes and alkynes

2,2,2-Trifluoroethylation of alkenes and alkynes with 2,2,2- trifluoroethyl iodide or bromide and sodium dithionite in DMSO or CH3CN/H2O can occur under mild conditions.

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The activation of carbon-chlorine bonds in per- and polyfluoroalkyl chlorides: DMSO-induced hydroperfluoroalkylation of alkenes and alkynes with sodium dithionite

In DMSO, the addition reactions of perfluoroalkyl chlorides, R(F)Cl, to alkenes or alkynes can occur smoothly in the presence of 1.5 equiv of Na2S2O4 and NaHCO3 at 75-80 °C for 4-10 h to give the corresponding adducts (RCH2CH2RF or RCH = CHR(F)). Ethyl chlorofluoro- (1f), chlorodifluoro- (1g) acetates, even nonfluorinated compounds, such as ethyl dichloro- (1h), chloro- (1i) acetates, and chloroform (1j) can undergo the similar reaction. Treatment of ω-iodo (or chloro-) perfluoroalkyl chlorides [X(CF2)(n) Cl, n = 2, 4, X= I or Cl] with > 3 equiv of alkenes and Na2SO4 gives directly the symmetrically disubstituted alkanes (RCH2CH2)2(CF2)(n). The symmetrically and unsymmetrically disubstituted adducts RCH2CH2(CF2)(n)CH2CH2R' from ω-iodoperfluoroalkyl chlorides can be also obtained stepwise, i.e., through the further addition reactions of monoadducts, RCH2CH2(CF2)(n)Cl to olefins. However, for α,ω- dichloroperfluoroalkanes, the similarly stepwise reactions with an alkene is not clean, both bis-adducts and the corresponding ω-hydrides, RCH2CH2(CF2)(n)H as byproducts are also formed. In the absence of alkenes or alkynes, per- and polyfluoroalkyl chlorides can be converted to their sulfinate salts and sulfonyl chlorides.

Amine-Stabilized Sulfenes, their Synthesis and Structure

The synthesis of quinuclidine-stabilized sulfene of the type XCH2-SO2-C(Y)=SO2- + (5a-d), whereas the corresponding methyl quinuclidinium salts (6a, b) are formed under methanolysis.