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

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.

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