(Bromodifluoromethyl)trimethylsilane

Base Information

• Chemical Name: (Bromodifluoromethyl)trimethylsilane
• CAS No.: 115262-01-6
• Molecular Formula: C4H9BrF2Si
• Molecular Weight: 203.102
• Hs Code.: 29319090
• European Community (EC) Number: 806-938-4
• Nikkaji Number: J823.673I
• Mol file: 115262-01-6.mol

Synonyms:(bromodifluoromethyl)trimethylsilane

Chemical Property of (Bromodifluoromethyl)trimethylsilane

Chemical Property:

• Refractive Index: n/D1.407
• Boiling Point: 108°C(lit.)
• Flash Point: 46℃
• PSA: 0.00000
• Density: 1.306
• LogP: 3.27140
• Storage Temp.: -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 201.96250
• Heavy Atom Count: 8
• Complexity: 86.5

Purity/Quality:

97% ^*data from raw suppliers

Trimethyl(bromodifluoromethyl)silane ^*data from reagent suppliers

Safty Information:

• Statements: 11
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C(F)(F)Br
• General Description: TriMethyl(broModifluoroMethyl)silane, also known as (Bromodifluoromethyl)trimethylsilane or Bromodifluoro(trimethylsilyl)methane, is a reagent used as a source of difluorocarbene in synthetic chemistry. It plays a key role in the copper-catalyzed allylation of α,α-difluoro-substituted organozinc reagents, enabling the efficient formation of CF2-containing compounds under mild conditions. This reagent facilitates the insertion of difluorocarbene into carbon-zinc bonds, contributing to the synthesis of organofluorine compounds with potential applications in medicinal chemistry due to the bioisosteric properties of the CF2 group. Its utility is highlighted in reactions involving functional group tolerance and the formation of complex fluorinated molecules.

Technology Process of (Bromodifluoromethyl)trimethylsilane

There total 2 articles about (Bromodifluoromethyl)trimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

chloro-trimethyl-silane (75-77-4) + halon-1211 (353-59-3) → bromodifluoromethane (1511-62-2) + Chlorodifluoromethane (75-45-6) + trimethylsilyl fluoride (420-56-4) + [bromo(difluoro)methyl]-trimethyl-silane (115262-01-6) + [chloro(difluoro)methyl]trimethylsilane (115262-00-5)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; aluminium; Mechanism; Product distribution; Ambient temperature; various reactant ratio, other temperature, ultrasound promotion;

DOI:10.1021/ja962990n

Reference yield:

chloro-trimethyl-silane (75-77-4) + dibromodifluoromethane (75-61-6) → [bromo(difluoro)methyl]-trimethyl-silane (115262-01-6) + [chloro(difluoro)methyl]trimethylsilane (115262-00-5)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; aluminium; Ambient temperature;

DOI:10.1021/ja962990n

Reference yield: 93.0%

C20H21NO2 + [bromo(difluoro)methyl]-trimethyl-silane (115262-01-6) → C21H21F2NO2

Guidance literature:

C₂₀H₂₁NO₂; With lithium hydroxide; In toluene; at 15 ℃; for 0.0833333h;

[bromo(difluoro)methyl]-trimethyl-silane; In toluene; at 15 ℃; for 24h; regioselective reaction;

DOI:10.1055/a-1507-5878

upstream raw materials:

chloro-trimethyl-silane

halon-1211

dibromodifluoromethane

Downstream raw materials:

[chloro(difluoro)methyl]trimethylsilane

1,1-difluoro-1-iodo-2-phenylethane

C₈H₇BrF₂Zn

1-bromo-2-(2,2-difluoro-2-iodoethyl)benzene

Refernces

Copper-catalyzed allylation of a,a-difluoro-substituted organozinc reagents

10.1021/jo4024705

The research explores a method for synthesizing CF2-containing compounds from three components: organozinc reagents, difluorocarbene, and allylic electrophiles. The purpose is to develop a more efficient and mild synthetic route for creating organofluorine compounds, which are of increasing interest in medicinal chemistry due to the CF2 fragment's ability to act as a bioisoster of ether oxygen and a carbonyl group. The study concludes that the reaction, involving the insertion of difluorocarbene into the carbon-zinc bond followed by copper-catalyzed allylic substitution, successfully forms two C-C bonds in one step under mild conditions. Key chemicals used include (Bromodifluoromethyl)trimethylsilane as a source of difluorocarbene, various organozinc reagents like methoxycarbonylbenzylzinc bromide, and allylic electrophiles such as allyl bromide and allyl chloride. The presence of copper (I) salts, specifically copper iodide, was crucial for inducing the zinc/copper exchange and facilitating the coupling reaction. The method demonstrated good tolerance for functional groups like esters and nitriles and provided products in good yields, highlighting its potential for practical applications in synthesizing complex fluorinated molecules.