808601
(Bromodifluoromethyl)trimethylsilane
98%
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About This Item
Empirical Formula (Hill Notation):
C4H9BrF2Si
CAS Number:
Molecular Weight:
203.10
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
MDL number:
Product Name
(Bromodifluoromethyl)trimethylsilane, 98%
InChI key
WDZVWBWAUSUTTO-UHFFFAOYSA-N
SMILES string
C[Si](C)(C(F)(F)Br)C
InChI
1S/C4H9BrF2Si/c1-8(2,3)4(5,6)7/h1-3H3
description
Flash point: 46.4°C
assay
98%
form
liquid
refractive index
n/D 1.407
density
1.306
storage temp.
−20°C
Application
(Bromodifluoromethyl)trimethylsilane may be used in the preparation of:
- gem-difluorocyclopropa(e)nes
- O-, S-, N-, and P-difluoromethylated compounds
- (chlorodifluoromethyl)trimethylsilane
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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
115.5 °F
flash_point_c
46.4 °C
Regulatory Information
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Recent advances in the synthetic application of difluorocarbene.
Ni C and Hu J.
Synthesis, 46(07), 842-863 (2014)
Nucleophilic Bromodifluoromethylation of Iminium Ions.
Tsymbal AV, et al.
The Journal of Organic Chemistry, 79(17), 7831-7835 (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
Prof. Jinbo Hu's lab focuses on developing new fluorination reagents and reactions, including difluoromethylation and monofluoromethylation.
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