333-47-1

Basic information

• Product Name: 4-(TRIFLUOROMETHYLTHIO)BROMOBENZENE
• Synonyms: 1-BROMO-4-(TRIFLUOROMETHYLTHIO)BENZENE;4-(TRIFLUOROMETHYLTHIO)BROMOBENZENE;4-BROMOPHENYL TRIFLUOROMETHYL SULFIDE;4-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE;P-BROMOPHENYL TRIFLUORO METHYLULFIDE;4-Bromophenyl trifluoromethyl sulphide 97%;4-Bromophenyltrifluoromethylsulphide97%;4-Bromophenyl trifluoromethyl sulfide,99%
• CAS NO: 333-47-1
• Molecular Formula: C₇H₄BrF₃S
• Molecular Weight: 257.07
• EINECS: -0
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds;Fluorine series
• Mol File: 333-47-1.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 199-200 °C(lit.)
• Flash Point: 182 °F
• Appearance: Clear colorless to slightly yellow liquid
• Density: 1.710 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.52mmHg at 25°C
• Refractive Index: n20/D 1.5130(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Stench
• BRN: 2361926
• CAS DataBase Reference: 4-(TRIFLUOROMETHYLTHIO)BROMOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYLTHIO)BROMOBENZENE(333-47-1)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYLTHIO)BROMOBENZENE(333-47-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 333-47-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

InChI:InChI=1/C7H4BrF3S/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

Upstream product

• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 75-63-8 Bromotrifluoromethane 
• 106-53-6 para-bromobenzenethiol 
• 5467-74-3 4-Bromophenylboronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 4589-43-9 1-bromo-4-[(trifluoromethane)sulfinyl]benzene 
• 589-87-7 1,4-bromoiodobenzene 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 34176-08-4 sodium 4-bromobenzenesulfinate 
• 56075-37-7 1-(methylsulfonyl)-2-(4-bromophenyl)diazene 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 183677-71-6 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1640084-14-5 (((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane) 
• 108-86-1 bromobenzene 

Downstream Products

• 312-20-9 1-bromo-4-(trifluoromethylsulfonyl)benzene 
• 765937-67-5 5-(4-trifluoromethylsulfanylphenyl)furan-2-carbaldehyde 
• 1333415-78-3 N-phenyl-4-((trifluoromethyl)thio)aniline 
• 330-14-3 4-(trifluoromethylthio)benzoyl chloride 
• 88489-60-5 methyl 4-[(trifluoromethyl)thio]benzoate 

Relevant articles and documents

Electrochemical initiation by sulfur dioxide of radical-chain trifluoromethylation processes of thiophenols with bromotrifluoromethane

Sulfur dioxide may serve as an efficient catalyst for the electrochemical trifluoromethylation of thiophenols by Freon F13B1 (CF3Br), which enables implementation of trifluoromethylation in an energy-saving radical-chain regime. - Keywords: Electrochemical trifluoromethylation; Thiophenols; Radical-chain processes; Bromotrifluoromethane; Sulfur dioxide catalyst

Radical Aromatic Trifluoromethylthiolation: Photoredox Catalysis vs. Base Mediation

Trifluoromethyl aryl sulfides (Ar-SCF3) constitute highly attractive building blocks due to their exceptional lipophilicity and chemical properties. Related protocols of radical aromatic trifluoro-methylthiolation of arenediazonium salts were developed that are based on the facile generation of intermediate aryl radicals. Their reactions with commercial F3CS-SCF3 under very mild conditions afforded a diverse set of Ar-SCF3 (3]Cl2} with the weak base-mediated dark reaction documented higher synthetic efficiency of the former but higher operational simplicity of the latter strategy.

Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

The first C?SCF3/SeCF3 cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochemical research and development.

Metal-Free Trifluoromethylthiolation of Arylazo Sulfones

A visible-light-driven protocol for the synthesis of aryl trifluoromethyl thioethers under photocatalyst- and metal-free conditions has been pursued. The procedure exploits the peculiar properties of arylazo sulfones (having electron-rich or electron-poor substituents on the (hetero)aromatic ring) as photochemical precursors of aryl radicals and S-trifluoromethyl arylsulfonothioates as easy-to-handle trifluoromethylthiolating agents.