16184-89-7

Basic information

• Product Name: 4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE
• Synonyms: 4-BROMO-ALPHA,ALPHA,ALPHA-TRIFLUOROACETOPHENONE;4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE;4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE, >=98%;1-(4-Bromophenyl)-2,2,2-trifluoroethanone;4-bromo-α,α,α-trifluoroacetophenone;4'-Bromo-2,2,2-trifluoroacetophenone 99%;1-(4-broMophenyl)-2,2,2-trifluoro-1-ethanone;1-(4-Bromophenyl)-2,2,2-trifluoroethan-1-one
• CAS NO: 16184-89-7
• Molecular Formula: C₈H₄BrF₃O
• Molecular Weight: 253.02
• EINECS: 1592732-453-0
• Product Categories: Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Fluorine series
• Mol File: 16184-89-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 26-30 °C(lit.)
• Boiling Point: 95 °C4 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: pale yellow transparent liquid
• Density: 1.662 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0845mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1956460
• CAS DataBase Reference: 4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(16184-89-7)
• EPA Substance Registry System: 4'-BROMO-2,2,2-TRIFLUOROACETOPHENONE(16184-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16184-89-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear light yellow liquid

Uses

4?-Bromo-2,2,2-trifluoroacetophenone may be used in the preparation of carbonyl-bridged bithiazole derivatives. Also used as a reagent to synthesize MK-5046, a selective Bombesin receptor subtype-3 agonist used to treat obesity.

InChI:InChI=1/C10H9F3O/c1-2-9(14)7-5-3-4-6-8(7)10(11,12)13/h3-6H,2H2,1H3

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 22480-64-4 4-bromophenyllithium 
• 106-37-6 1.4-dibromobenzene 
• 80418-12-8 1-(4-bromo-phenyl)-2,2,2-trifluoro-ethanol 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 586-75-4 4-chlorobenzoyl chloride 
• 104863-67-4 N-methoxy-N-methyltrifluoroacetamide 
• 340-07-8 N-(trifluoroacetyl)piperidine 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 1122-91-4 4-bromo-benzaldehyde 
• 16261-79-3 O₂NCF₂C(4-Br-C₆H₄)(OH)CF₃ 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 80418-12-8 1-(4-bromo-phenyl)-2,2,2-trifluoro-ethanol 
• 80418-12-8 (R)-1-(4-bromophenyl)-2,2,2-trifluoroethanol 
• 76911-73-4 (S)-1-(4-bromophenyl)-2,2,2-trifluoroethan-1-ol 
• 70783-32-3 2,2,2-trifluoro-1-(4-phenoxyphenyl)-ethanone 
• 1011484-02-8 N-[(1R)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-S-methyl-L-cysteine 
• 1011484-01-7 N-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-S-methyl-L-cysteine 
• 935265-36-4 1-(4-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone 
• 945428-26-2 1-(1-(4-bromophenyl)-2,2,2-trifluoroethylidene)hydrazine 
• 292145-64-3 1-(4-bromophenyl)-2,2,2-trifluoroethanone oxime 
• 122243-28-1 2‐(4‐bromophenyl)‐1,1,1‐trifluoropropan‐2‐ol 
• 1064622-26-9 (2R,4S)-2-(4-bromophenyl)-4-(2-fluoro-2-methylpropyl)-2-(trifluoromethyl)-1,3-oxazolidine 

Relevant articles and documents

Enantioselective Synthesis of Trifluoromethyl α,β-Unsaturated δ-Lactones via Vinylogous Aldol-Lactonization Cascade

The novel vinylogous aldol-lactonization cascade of alkylidene oxindole with trifluoromethyl ketones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of alkylidene oxindoles for the preparation of enantioenriched trifluoromethylated α,β-unsaturated δ-lactones.

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

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.