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808601

Sigma-Aldrich

(Bromodifluoromethyl)trimethylsilane

98%

Empirical Formula (Hill Notation):
C4H9BrF2Si
CAS Number:
Molecular Weight:
203.10
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

description

Flash point: 46.4°C

assay

98%

form

liquid

refractive index

n/D 1.407

density

1.306

storage temp.

−20°C

SMILES string

C[Si](C)(C(F)(F)Br)C

InChI

1S/C4H9BrF2Si/c1-8(2,3)4(5,6)7/h1-3H3

InChI key

WDZVWBWAUSUTTO-UHFFFAOYSA-N

Related Categories

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.

Application

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.
(Bromodifluoromethyl)trimethylsilane may be used in the preparation of:
  • gem-difluorocyclopropa(e)nes
  • O-, S-, N-, and P-difluoromethylated compounds
  • (chlorodifluoromethyl)trimethylsilane

Packaging

1 g in glass bottle

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

115.5 °F

Flash Point(C)

46.4 °C

Certificate of Analysis

Certificate of Origin

Nucleophilic Bromodifluoromethylation of Iminium Ions.
Tsymbal AV, et al.
The Journal of Organic Chemistry, 79(17), 7831-7835 (2014)
Recent advances in the synthetic application of difluorocarbene.
Ni C and Hu J.
Synthesis, 46(07), 842-863 (2014)
Synthesis of gem-Difluorocyclopropa (e) nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF2Br.
Li L, et al.
Angewandte Chemie (International Edition in English), 52(47), 12390-12394 (2013)
Coupling of a,a-difluoro-substituted organozinc reagents with 1-bromoalkynes.
Zemtsov AA, et al.
Beilstein Journal of Organic Chemistry, 11(1), 2145-2149 (2015)

Related Content

Hu Group – Professor Product Portal

The major research interests of Prof. Jinbo Hu's lab include the development of new fluorination reagents and reactions, especially the difluoromethylation, difluoromethylenation, and monofluoromethylation methods.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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