655-26-5

Basic information

• Product Name: 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE
• Synonyms: 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE;3'-Bromo-2,2,2-trifluoroacetophenone 98%;1-(3-Bromophenyl)-2,2,2-trifluoroethan-1-one;1-(3-broMophenyl)-2;2-trifluoroethanone;3-Bromo-ααα-trifluoroacetophenone;3-Brom-α,α,α-trifluoracetophenon;3'-Bromo-2,2,2-trifluoroacetophenone >=97%
• CAS NO: 655-26-5
• Molecular Formula: C₈H₄BrF₃O
• Molecular Weight: 253.02
• Product Categories: Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 655-26-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 235.626°C at 760 mmHg
• Flash Point: 96.304°C
• Appearance: /
• Density: 1.637g/mLat 25℃
• Vapor Pressure: 0.05mmHg at 25°C
• Refractive Index: n20/D 1.504
• Storage Temp.: 2-8°C
• BRN: 2329910
• CAS DataBase Reference: 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(655-26-5)
• EPA Substance Registry System: 3'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(655-26-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 655-26-5(Hazardous Substances Data)

Usage

Uses

3'-Bromo-2,2,2-trifluoroacetophenone is a useful research chemical.

InChI:InChI=1/C8H4BrF3O/c9-6-3-1-2-5(4-6)7(13)8(10,11)12/h1-4H

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 108-36-1 1,3-dibromobenzene 
• 75-46-7 trifluoromethan 
• 618-89-3 methyl 3-bromobenzoate 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 591-18-4 1-Bromo-3-iodobenzene 
• 24398-88-7 ethyl 3-bromobenzoate 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 3132-99-8 m-bromobenzoic aldehyde 
• 207681-67-2 N-methoxy-N-methyl-3-bromobenzamide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 446-63-9 (±)-1-(3-bromophenyl)-2,2,2-trifluoroethanol 
• 111762-31-3 3-bromophenyl magnesium bromide 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 878408-46-9 (R)-2,2,2-trifluoro-1-(3-bromophenyl)ethylamine hydrochloride 
• 878408-46-9 (S)-2,2,2-trifluoro-1-(3-bromophenyl)ethylamine hydrochloride 
• 1617507-20-6 (S)-12-(3-bromophenyl)-12-trifluoromethyl-5,6,11,12-tetrahydrobenzo[2,3]azepino[5,6-b]indole 
• 1631143-21-9 2-((1H-indol-2-yl)methyl)-N-(1-(3-bromophenyl)-2,2,2-trifluoroethylidene)aniline 

Relevant articles and documents

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at ?40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.

Fluoroform: an Efficient Precursor for the Trifluoromethylation of Aromatic Esters by Sodium Diisopropylamide with Trialkylamines

The trifluoromethanide anion is the postulated key intermediate in nucleophilic trifluoromethylation reactions. It is believed to be incompatible with Na+ cation due to the strong Na–F bond. However, herein we demonstrate that it could be prepared for the first time. Trialkylamines can be used as cation chelating agents to stabilize the isolated –CF3 ion to realize trifluoromethylation reaction. With this strategy, trifluoromethyl aromatic ketones could be effectively synthesized from fluoroform and aromatic esters with diisopropyl aminosodium (NaDA) and trialkylamines.

Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.