115262-00-5

Basic information

• Product Name: (chlorodifluoroMethyl)triMethylsilane
• Synonyms: (chlorodifluoroMethyl)triMethylsilane
• CAS NO: 115262-00-5
• Molecular Formula: C₄H₉ClF₂Si
• Molecular Weight: 158.6495664
• Product Categories: Aliphatics, Miscellaneous Reagents, Sulfur & Selenium Compounds
• Mol File: 115262-00-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 90.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.039±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (chlorodifluoroMethyl)triMethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (chlorodifluoroMethyl)triMethylsilane(115262-00-5)
• EPA Substance Registry System: (chlorodifluoroMethyl)triMethylsilane(115262-00-5)

Safety Data

• Statements: 11
• Safety Statements: 24/25
• TSCA: No
• Hazardous Substances Data: 115262-00-5(Hazardous Substances Data)

Usage

Uses

(Chlorodifluoromethyl)trimethylsilane, is one of the partially fluorinated compounds, which are often used for diverse applications in materials science, agrochemistry, and the pharmaceutical industry.

Upstream product

• 115262-01-6 [bromo(difluoro)methyl]-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 75-61-6 dibromodifluoromethane 
• 353-59-3 halon-1211 

Downstream Products

• 420-56-4 trimethylsilyl fluoride 
• 65864-64-4 trimethyl(difluoromethyl)silane 
• 86847-53-2 bis(trimethylsilyl)difluoromethane 
• 186824-44-2 1,2-bis(trimethylsilyl)-1,1,2,2-tetrafluoroethane 
• 107-46-0 Hexamethyldisiloxane 
• 1427-33-4 1,1,2-trifluoro-2-trimethylsilylethylene 
• 6312-18-1 2-chloro-2,2-difluoro-1,1-diphenyl-ethanol 
• 145299-88-3 1-benzyl-2-chloro-2,2,-difluoroethanol 
• 55991-66-7 1-(4-bromophenyl)-1-(trimethylsilyloxy)ethylene 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 38858-72-9 1-trimethylsiloxy-3,4-dihydronaphthalene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 74812-79-6 1-(4-nitrophenyl)-1-trimethylsilyloxyethylene 

Relevant articles and documents

Fluorierte Elementorganika XX. Synthese von Fluormethyltrimethylsilanen

The synthesis of the fluoromethyltrimethylsilanes 4 > is described.The reaction of the tris-(diethylamino)-phosphane (1)/trimethylsilylhalogenide 3 system with the difluorodihalogenomethanes 2 gives the hitherto unknown 4a,b.The reduction of 4a,b and dichlorofluoromethyltrimethylsilane (13) with tris-(n-butyl)stannane (14) produces 4c-e in fair yields.

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

Background: 1,1-Difluoroalkenes cannot only be used as valuable precursors for organic synthesis, but also act as bioisosteres for enzyme inhibitors. Among various methods for their preparation, the carbonyl olefination with difluoromethylene phosphonium ylide represents one of the most straightforward methods. Results: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane (TMSCF3) in this reaction. Conclusion: Similar to many other Wittig-type gem-difluoroolefination reactions in the presence of PPh3, the reaction of TMSCF2Cl with aldehydes and activated ketones is effective.

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).