(Difluoromethyl)trimethylsilane

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem SID
Reaxys RN
Trimethyl(difluoromethyl)silane,TMSCF2H,Me3SiCF2H
Difluoromethylating Reagents
KUMI2F24
65864-64-4
MFCD19381658
329765673
2423974
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay
Appearance
Boiling Point
Packaging
Storage
(Difluoromethyl)trimethylsilane
C4H10F2Si
124.20
≥98%(GC)
Colorless Clear Liquid
65-66ºC
5g,10g,25g,50g,100g,500g and 1kg
Store 2-8ºC (recommended)
(Difluoromethyl)trimethylsilane(TMSCF2H,Me3SiCF2H) is a versatile and non-hazardeous fluorine source for the late-stage difluoromethylation of various aldehydes, ketones, and imines, through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. It also can be used as difluoromethylthiolating reagent to efficiently and directly introduce the important lipophilic hydrogen-bond donor motif(SCF2H) to corresponding compounds. Such difluoromethylthiolated compounds are very useful in materials science and medicinal and agricultural chemistry.
Difluoromethylation of Carbonyl Compounds with (Difluoromethyl)trimethylsilane. [1]
Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H. [2]
Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ. [3]
Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H. [4]
Direct nucleophilic difluoromethylation of enolizable ketones with CHF2TMS/HMPA. [5]
References:
[1] A.A.Tyutyunov,V.E.Boyko, S.M.Igoumnov, Fluorine Notes, 2011, 5(78).
[2] Y.Zhao, W.Huang, J. Zhang, J.Hu, Org. Lett., 2011, 13(19), pp 5342-5345.
[3] B.Bayarmagnai, C.Matheis, K.Jouvin, L.J.Goossen, Angew.Chem.Int.Ed.Engl., 2015, 54(19), pp 5753-5756.
[4] J.L.Howard, C.Schotten, S.T. Alston, D.L. Browne, Chem. Commun., 2016, 52(54), pp 8448-8451.
[5] O.M. Michurin, D.S. Radchenko, I.V.Komarov, Tetrahedron, 2016, 72(10), pp 1351-1356.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Danger
H225
P210
2931.90.9010
UN 1993  3/PG II

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