312-20-9

Basic information

• Product Name: 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene
• Synonyms: 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene
• CAS NO: 312-20-9
• Molecular Formula: C₇H₄BrF₃O₂S
• Molecular Weight: 289
• Mol File: 312-20-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 64-65 °C(Solv: ethanol (64-17-5))
• Boiling Point: 292°C at 760 mmHg
• Flash Point: 130.4°C
• Appearance: /
• Density: 1.764g/cm³
• Vapor Pressure: 0.00328mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene(312-20-9)
• EPA Substance Registry System: 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene(312-20-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 312-20-9(Hazardous Substances Data)

Usage

General Description

1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is a chemical compound with the molecular formula C7H4BrF3O2S. It is a white to light yellow crystalline solid that is primarily used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is also employed as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is known for its ability to undergo various chemical reactions, including nucleophilic substitution, palladium-catalyzed cross-coupling, and Suzuki-Miyaura coupling reactions, making it a versatile building block for the production of complex organic molecules. However, it is important to handle this compound with care, as it is considered harmful if swallowed, inhaled, or in contact with skin, and can cause irritation to the respiratory system and skin.

InChI:InChI=1/C7H4BrF3O2S/c8-5-1-3-6(4-2-5)14(12,13)7(9,10)11/h1-4H

Upstream product

• 473-27-8 4-(trifluoromethanesulfonyl)aniline 
• 333-47-1 1-bromo-4-(trifluoromethyl)thiobenzene 
• 106-53-6 para-bromobenzenethiol 
• 432-87-1 1-nitro-4-(trifluoromethylsulfonyl)benzene 
• 56456-52-1 (4-((trifluoromethyl)thio)phenyl)methanol 
• 219872-98-7 4-(trifluoromethylsulfonyl)benzyl alcohol 
• 25752-90-3 tert-butyl 4-bromophenyl sulfide 
• 2926-29-6 Langlois reagent 
• 75-46-7 trifluoromethan 
• 498-83-9 4-bromobenzenesulfonyl fluoride 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 1203709-75-4 4-bromo-2,4,6-trimethyldiphenyliodonium trifluoromethanesulfonate 
• 1242069-27-7 trifluoromethanesulfonic acid 4-bromo-2-trimethylsilanyl-phenyl ester 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 933038-06-3 trimethyl[[4-[(trifluoromethyl)sulfonyl]phenyl]ethynyl]silane 
• 671-70-5 Trifluormethyl-(4-brom-3-nitro-phenyl)-sulfon 
• 351903-73-6 1-ethynyl-4-[(trifluoromethyl)sulfonyl]benzene 
• 797-09-1 2-(2-bromo-phenylsulfanyl)-5-trifluoromethanesulfonyl-aniline 
• 1763-73-1 N-[2-(2-bromo-phenylsulfanyl)-5-trifluoromethanesulfonyl-phenyl]-formamide 
• 648904-89-6 4,4,5,5-tetramethyl-2-(4-((trifluoromethyl)sulfonyl)phenyl)-1,3,2-dioxaborolane 
• 845616-92-4 1-(4-Trifluoromethanesulfonyl-phenyl)-piperazine 
• 63708-74-7 2-(4-trifluoromethylsulfonylphenylthio)benzoic acid 
• 1034822-28-0 tert-butyl 1'-{4-[(trifluoromethyl)sulfonyl]phenyl}-4,4'-bipiperidine-1-carboxylate 

Relevant articles and documents

Synthesis and nicotinic acetylcholine receptor in vitro and in vivo pharmacological properties of 2′-fluoro-3′-(substituted phenyl)deschloroepibatidine analogues of 2′-fluoro-3′-(4- nitrophenyl)deschloroepibatidine

Herein, we report the synthesis and nicotinic acetylcholine receptor (nAChR) in vitro and in vivo pharmacological properties of 2′-fluoro- 3′-(substituted phenyl)deschloroepibatidines 5b-g, analogues of 3′-(4-nitrophenyl) compound 5a. All compounds had hi

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

SuFEx is a new-generation click chemistry transformation that exploits the unique properties of S?F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx-based procedure for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new process involves rapid S?F exchange with trifluoromethyltrimethylsilane (TMSCF3) upon activation by potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative mechanism is proposed involving nucleophilic displacement of S?F by the trifluoromethyl anion via a five-coordinate intermediate. The utility of late-stage SuFEx trifluoromethylation is demonstrated through the synthesis and selective anticancer properties of a bis(trifluoromethyl)sulfur oxyimine.

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).