[Difluoro(phenylthio)methyl]trimethylsilane

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem CID
Reaxys RN
Me3SiCF2SPh,Phenyl (trimethylsilyl)difluoromethyl sulfide
Difluoromethylating Reagents
KUMI2F19
536975-49-2

11075297
9478571
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay
Appearance
Boiling Point
Packaging
Storage
[Difluoro(phenylthio)methyl]trimethylsilane
C10H14F2SPh
232.27
≥98%(GC)
Yellow Liquid
86-87ºC(4 Torr)
1ml,5ml,10ml and 50ml
Store at room temperature
An effective reagent to introduce difluoromethyl groups into carbonyls, imines, enamines, and alkyl halides. Not only various simple aldehydes and ketones, but also functionalized carbonyls such as α- and γ-ketoesters and cyclic imides can be difluoro(phenylthio)methylated in high yields
under the activation of a catalytic amount of Lewis bases. The substitution reaction proceeds well with primary alkyl bromides and iodides as the limiting reactant when cesium fluorode/15-crown-5 is used as the fluoride source/additive.

Under radical conditions, the difluoro(phenylthio)methyl compounds containing vinyl functional groups can form 5- or 6-membered rings via intramolecular cyclization.
Stereoselective Difluoromethylenation Using Me3SiCF2SPh: Synthesis of Chiral 2,4-Disubstituted 3,3-Difluoropyrrolidine. [1]
Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides followed by radical cyclization: General synthetic strategy of gem-difluoromethylenated 1-azabicyclic compounds.  [2]
Reactions of sulfur- and phosphorus-substituted fluoroalkylating silicon reagents with imines and enamines under acidic conditions. [3]
Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: Synthesis of γ-difluoromethylated γ-lactams.[4]
Stereoselective Nucleophilic Addition of PhSCF2SiMe3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem-Difluoromethylenated Polyhydroxypyrrolizidines and -indolizidines.[5]
References:
[1] Y. Li, J. Hu, Angew. Chem. Int. Ed., 2007, 46(14), pp 2489-2492.
[2] T. Bootwicha, D. Panichakul, C. Kuhakarn, S. Prabpai, P. Kongsaeree, P. Tuchinda, V. Rentrakul, M. Pohmakotr, J.Org. Chem., 2009, 74(10), pp 3798-3805.
[3] M.D.Kosobokov, A.D.Dilman, M. I. Struchkova, P.A. Belyakov,J.Hu, J. Org. Chem., 2012,77(4),pp 2080-2086.
[4] V. Pharikronburee, T. Punirun,D. Soorukram, C. Kuhakarn,P. Tuchinda, V. Reutrakul, M. Pohmakotr, Org. Biomol. Chem., 2013, 11, pp 2022-2033.
[5] K.Korvorapun, D. Soorukram, C. Kuhakarn, P. Tuchinda, V. Reutrakul, M. Pohmakotr, Chem. : An Asian J., 2015, 10(4), pp 948-968.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Warning
H226,H315,H319,H335
P210,P305+P351+P338,P370+P378
2931.39.9090
UN 1993C 3/PG II

1. Product Specification
2. Safety Data Sheet
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