536975-49-2

Basic information

• Product Name: [[difluoro(triMethylsilyl)Methyl]thio]-Benzene
• Synonyms: [[difluoro(triMethylsilyl)Methyl]thio]-Benzene;[Difluoro(phenylthio)Methyl]triMethylsilane;[Difluoro(phenylsulfanyl)methyl]trimethylsilane
• CAS NO: 536975-49-2
• Molecular Formula: C₁₀H₁₄F₂SSi
• Molecular Weight: 232.3654664
• Mol File: 536975-49-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 208.986 °C at 760 mmHg
• Flash Point: 80.192 °C
• Appearance: /
• Density: 1.074 g/cm³
• Solubility: soluble in most organic solvents, for example hexane, tetrahydrofuran (THF), CH2Cl2, dimethylformamide (DMF), and so on.
• CAS DataBase Reference: [[difluoro(triMethylsilyl)Methyl]thio]-Benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [[difluoro(triMethylsilyl)Methyl]thio]-Benzene(536975-49-2)
• EPA Substance Registry System: [[difluoro(triMethylsilyl)Methyl]thio]-Benzene(536975-49-2)

Safety Data

• Hazardous Substances Data: 536975-49-2(Hazardous Substances Data)

Usage

Physical properties

colorless liquid; bp 86–87?C/4 mmHg.

Uses

Organofluorine compounds have received remarkable interest in recent years due to their wide-ranging biological effects. The development of general synthetic routes to such compounds and the use of new fluorinated compounds as building blocks are of great importance. Of particular interest is the selective incorporation of the gem-difluoromethylene group ‘CF2’ into organic molecules. The report on the synthesis of PhSCF2SiMe3 was published in 2003 by Prakash et al., and the reagent has become one of the most versatile and efficient nucleophilic (phenylthio)difluoromethylating reagents.When excess potassium t-butoxide was used as a promoter, PhSCF2SiMe3 reacted with diphenyl disulfide to give the corresponding dithioacetal in 85% yield (eq 8).

Preparation

[difluoro(phenylthio)methyl]trimethylsilane (PhSCF2SiMe3) was prepared for the first time by Prakash et al.,1 using the Barbier coupling reaction of bromodifluoromethylphenyl sulfide,2 prepared from dibromodifluoromethane and sodium benzenethiolate,3 magnesium metal, and chlorotrimethylsilane (TMSCl) in DMF (eq 1).

Upstream product

• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 108-98-5 thiophenol 
• 78031-08-0 [(bromodifluoromethyl)sulfanyl]benzene 
• 930-69-8 sodium thiophenolate 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 899820-42-9 1,1-difluoro-4-phenyl-1-phenylsulfanyl-2-trimethoxysiloxy-3-butene 
• 899820-47-4 2,2-difluoro-1-(4-bromophenyl)-2-phenylsulfanyl-1-trimethoxysiloxyethane 
• 899820-55-4 (1,1-difluoro-2-phenyl-1-phenylsulfanylpropan-2-oxy)trimethylsilane 
• 899820-41-8 1,1-difluoro-4-phenyl-1-phenylsulfanyl-3-buten-2-ol 

Relevant articles and documents

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(Benzenesulfonyl)difluoromethanesulfenamide (PhSO2-BB12H) is an interesting reagent to lead to various fluoroalkylselenotated molecules. This compound is obtained from [(benzenesulfonyl)difluoromethyl]trimethylsilane. Herein, a new process in two steps, w

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The invention relates to a process for preparing aromatic sulphonylimides, to the sulphonylimides obtained, and to the use thereof as salt of an electrolyte. The sulphonylimides correspond to the formula [R—SO2—N—SO2R′]rM (I). R′ is an ArZL- group. R′ is a perfluoroalkyl group or an ArZL- group. Z is an S, SO or SO2 group. L is a —(CF2)n—CFRf— group. n is 0 or 1; Rf represents F or a C1 to C8 perfluoroalkyl group; Ar is an aromatic group. M represents H, an alkali metal cation, an alkaline earth metal cation, a trivalent or tetravalent metal cation, or an organic cation. The process consists in preparing a compound RSO2N(R′)SO2R′ from RSO2F, and in replacing the group R′ by nucleophilic substitution reaction so as to obtain the compound (I), R′ being a benzyl or trimethylsilyl group.