115262-01-6

Basic information

• Product Name: TriMethyl(broModifluoroMethyl)silane
• Synonyms: TriMethyl(broModifluoroMethyl)silane;(BroModifluoroMethyl)triMethylsilane;(Bromodifluoromethyl)trimethylsilane 98%;Bromodifluoro(trimethylsilyl)methane;(Bromodifluoromethyl)
• CAS NO: 115262-01-6
• Molecular Formula: C₄H₉BrF₂Si
• Molecular Weight: 203.1005664
• EINECS: -0
• Mol File: 115262-01-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 108°C(lit.)
• Flash Point: 46℃
• Appearance: /
• Density: 1.306
• Refractive Index: n/D1.407
• Storage Temp.: -20°C
• CAS DataBase Reference: TriMethyl(broModifluoroMethyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: TriMethyl(broModifluoroMethyl)silane(115262-01-6)
• EPA Substance Registry System: TriMethyl(broModifluoroMethyl)silane(115262-01-6)

Safety Data

• Statements: 11
• Safety Statements: 24/25
• RIDADR: UN 1993C 3 / PGIII
• TSCA: No
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 115262-01-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 115262-01-6 differently. You can refer to the following data:
1. Novel difluorocarbene source for the efficient difluoromethylenation of alkenes/alkynes and difluoromethylation of O-, S-, and N-nucleophiles.
2. Trimethyl(bromodifluoromethyl)silane can be used as neuroactive steroids.
3. 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.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 353-59-3 halon-1211 
• 75-61-6 dibromodifluoromethane 

Downstream Products

• 126587-15-3 (2,2-difluoro-1-phenylcyclopropoxy)trimethylsilane 
• 506437-43-0 2-fluoro-1-(4-methoxyphenyl)-2-propen-1-one 

Relevant articles and documents

Preparation of and fluoroalkylation with (chlorodifluoromethyl)trimethylsilane, difluorobis(trimethylsilyl)methane, and 1,1,2,2-tetrafluoro-1,2-bis(trimethylsilyl)ethane

CF2BrCl reacts with aluminum/N-methylpyrrolidinone in the presence of chlorotrimethylsilane to give Me3SiCF2Cl in high yield. Similarly, CF2Br2 gives Me3SiCF2Br with bromotrimethylsilane. Chlorodifluoromethylation of aldehydes using Me3SiCF2Cl and a catalytic amount of TBAF in polar solvents occurs at room temperature, providing difluoromethylated alcohols in two steps. Electroreduction of Me3SiCF2Cl in the presence of chlorotrimethylsilane gives Me3SiCF2SiMe3 (anion-derived product) and Me3SiCF2CF2SiMe3 (radical-derived product). Using THF/HMPA strongly favors the former, whereas THF/TDA-1 (tris(3,6-dioxaheptyl)amine) the latter. Me3SiCF2SiMe3 difluoromethylates aldehydes acting as a difluoromethylene dianion ('CF22-'/equivalent), whereas Me3SiCF2CF2SiMe3 acts at room temperature as an in situ source for the perfluorovinyl anion (due to β-elimination of fluorotrimethylsilane). However, at low temperature the elimination pathway is suppressed and tetrafluoroethylene dianion ('-CF2CF2-'/equivalent) behavior is observed. The structure of Me3SiCF2CF2SiMe3 was analyzed by X-ray diffraction. All of the studied fluoroalkylating reagents are moisture- and air-stable and can be readily obtained from a single convenient precursor (CF2BrCl).