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TriMethyl(broModifluoroMethyl)silane

Product NameTriMethyl(broModifluoroMethyl)silane
CAS115262-01-6
MFC4H9BrF2Si
MW203.1
EINECS806-938-4
MOL File115262-01-6.mol

Chemical Properties

Boiling point	108°C(lit.)
Density	1.306
refractive index	n/D1.407
Flash point	46℃
storage temp.	-20°C
form	liquid
color	clear
InChIKey	WDZVWBWAUSUTTO-UHFFFAOYSA-N
CAS DataBase Reference	115262-01-6

Safety Information

Risk Statements	11
Safety Statements	24/25
RIDADR	UN 1993C 3 / PGIII
TSCA	No
HazardClass	3
PackingGroup	II
HS Code	29319090

Usage And Synthesis

Chemical Properties

Colorless transparent liquid, initial boiling point 108℃, relative density 1.31 g/cm³.

Uses

Novel difluorocarbene source for the efficient difluoromethylenation of alkenes/alkynes and difluoromethylation of O-, S-, and N-nucleophiles.

Uses

Trimethyl(bromodifluoromethyl)silane can be used as neuroactive steroids.

Uses

As reported by Hu and co-workers, (Bromodifluoromethyl)trimethylsilane is a highly useful reagent for the formation of difluoromethene-containing 3-membered rings and can also difluoromethylate heteroatoms with the assistance of alkaline bases, most effectively KOH.

Application

TriMethyl(broModifluoroMethyl)silane commonly can be used as a source for generating difluorocarbene, it is a general reagent with broad synthetic utility.
Can generate difluorocarbene under neutral/acidic/basic conditions in the presence/absence of water at low/high temperatures.
Can be used to prepare gem-difluorocyclopropan(e)nes, O-, S-, N-, and P-difluoromethylated compounds

Reactions

(1) Difluoromethylenation of TMSCN.
TriMethyl(broModifluoroMethyl)silane

Ref. J. Org. Chem. 2012, 77, 5850?5855.
(2) Difluoromethylenation of benzyl and alkylzinc halides.
TriMethyl(broModifluoroMethyl)silane

Ref. Org. Lett. 2013, 15, 917 – 919.
(3) Fluorination aminocarbonylation of aldehydes
TriMethyl(broModifluoroMethyl)silane

Ref. Angew. Chem. Int. Ed. 2022, e202115467

General Description

(Bromodifluoromethyl)trimethylsilane (TMSCF₂Br) is commonly used as a source to generate dilfluorocarbene. TMSCF₃ (Ruppert–Prakash reagent) and BBr₃ undergoes fast halogen–exchange reaction to form MSCF₂Br.

References

[1]Angewandte Chemie International Edition.DOI :10.1002/anie.202283811
[2]The Journal of Organic Chemistry.DOI :10.1021/acs.orglett.2c02899

TriMethyl(broModifluoroMethyl)silane

Chemical Properties

Safety Information

Usage And Synthesis

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