TriMethyl(broModifluoroMethyl)silane 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

TriMethyl(broModifluoroMethyl)silane 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.

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

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

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(115262-01-6)Related Product Information

• TRIMETHYLSILYL ISOCYANATE
• Trimethylboroxine
• TRIMETHYL(PENTAFLUOROPHENYL)SILANE
• (PENTAFLUOROETHYL)TRIMETHYLSILANE
• Trimethyl(nonafluorobutyl)silane
• (HEPTAFLUOROPROPYL)TRIMETHYLSILANE
• tert-butyl (S)-2-(trifluoromethyl)piperazine-1-carboxylate
• diethyl (2,4-difluorobenzyl)phosphonate
• (S)-3-Methyl-pyrrolidine-3-carboxylic acid
• di-tert-butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate
• (3S)-3-(TrifluoroMethyl)-1-piperazinecarboxylic acid 1,1-DiMethylethyl Ester
• Dicyclopentadiene diepoxide
• (PENTAFLUOROPHENYL)TRIETHOXYSILANE
• Chloromethyltrimethylsilane
• L-Alanine
• Phosphorus pentoxide
• 2-(Trimethylsilyl)ethoxymethyl chloride