709-63-7

Basic information

• Product Name: 4'-(Trifluoromethyl)acetophenone
• Synonyms: 1-(4-Trifluoromethyl-phenyl)-ethanone;1-[4-(Trifluoromethyl)phenyl]ethanone;Ethanone, 1-[4-(trifluoromethyl)phenyl]-;1-[4-(Trifluoromethyl)phenyl]ethan-1-one;4'-(TRIFLUOROMETHYL)ACETOPHENONE;4-(TRIFLUOROMETHYL)ACETOPHENONE;4-ACETYLBENZOFLUORIDE;4-ACETYLBENZOTRIFLUORIDE
• CAS NO: 709-63-7
• Molecular Formula: C₉H₇F₃O
• Molecular Weight: 188.15
• EINECS: 211-913-0
• Product Categories: Trifluoromethylbenzene serise;Aromatic Acetophenones & Derivatives (substituted);ketone;Aromatics
• Mol File: 709-63-7.mol
• Article Data: 211

Chemical Properties

• Melting Point: 30-33 °C(lit.)
• Boiling Point: 79-80 °C8 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: White to faintly yellow/Low Melting Solid
• Density: 0.92
• Vapor Pressure: 17.8mmHg at 25°C
• Refractive Index: 1.4604
• Storage Temp.: Flammables area
• BRN: 1870425
• CAS DataBase Reference: 4'-(Trifluoromethyl)acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(Trifluoromethyl)acetophenone(709-63-7)
• EPA Substance Registry System: 4'-(Trifluoromethyl)acetophenone(709-63-7)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-11
• Safety Statements: 26-36-37/39-16
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 709-63-7(Hazardous Substances Data)

Usage

Synthesis

41.6 g of chlorocyclohexane (0.35 mol) were added dropwise to a suspension of 4.65 g of lithium particles (0.68 mol) in 350 g of THF at -55 °C, and an addition time of 2 hours was chosen. After >97% chlorocyclohexane conversion by GC (10 hours), a mixture of 38.3 g of 4-bromotrifluorotoluene (0.170 mol) and 7.0 g of acetonitrile (0.170 mol) was added dropwise at the same temperature for 15 minutes. After stirring for an additional 30 minutes at -50°C, the reaction mixture was slowly thawed to room temperature and subjected to an aqueous workup in a conventional manner. The yield of 4-trifluoromethylacetophenone after distillation was 81%.

Uses

A labelled acetophenone with selective antimycobacterial activity.

General Description

The enantioselective addition of dialkylzinc to 4′-(trifluoromethyl)acetophenone mediated by 1,2-bis(hydroxycamphorsulfonamido)cyclohexenes in the presence of titanium tetraisopropoxide has been investigated. Phosphorescence emission spectra of 4′-(trifluoromethyl)acetophenone has been studied using pulsed source phosphorimetry.

Purification Methods

Purify the ketone by distillation or sublimation in vacuo.[Beilstein 7 IV 1404.]

InChI:InChI=1/C2H4BrF2N/c3-2(4,5)1-6/h1,6H2

Upstream product

• 1737-26-4 1-(4-trifluorophenyl)ethanol 
• 13329-40-3 4-Iodoacetophenone 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 42916-66-5 1-(4-(trifluoromethyl)phenyl)pentan-1-one 
• 107496-43-5 1-(4-(trifluoromethyl)phenyl)ethan-1-one O-methyl oxime 
• 343968-74-1 p-trifluoromethyl-δ-chlorovalerophenone 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 917-54-4 methyllithium 
• 75-63-8 Bromotrifluoromethane 
• 99-90-1 para-bromoacetophenone 
• 98-08-8 α,α,α-trifluorotoluene 
• 75-36-5 acetyl chloride 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 15996-83-5 1-[4-(trifluoromethyl)phenyl]ethanone oxime 

Downstream Products

• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 2252-62-2 2-(4-(trifluoromethyl)phenyl)propan-2-ol 
• 60820-06-6 2-(1-(4-(trifluoromethyl)phenyl)ethylidene)malononitrile 
• 78888-54-7 2-Piperidin-1-ylmethyl-1-(4-trifluoromethyl-phenyl)-propenone; hydrochloride 
• 117874-50-7 8-Methyl-2-(4-trifluoromethyl-phenyl)-quinoline-4-carboxylic acid 
• 906482-51-7 2-(4-Trifluoromethyl-phenyl)-2-trimethylsilanyloxy-propionitrile 
• 147218-05-1 2,5-bis(trifluoromethyl)-N-<1-<4-(trifluoromethyl)phenyl>ethylidene>aniline 
• 22707-48-8 p-Trifluormethylphenyl-tert.butyl-methyl-carbinol 
• 96307-88-9 2-(4-Trifluoromethyl-phenyl)-pent-3-yn-2-ol 
• 55186-75-9 4-trifluoromethyl-α-methylstyrene 
• 70205-64-0 1-(4-Trifluoromethyl-phenyl)-ethylidene-oxonium 
• 98-86-2 acetophenone 
• 27190-69-8 1-ethyl-4-(trifluoromethyl)benzene 
• 1737-26-4 1-(4-trifluorophenyl)ethanol 

Relevant articles and documents

Synthesis of a series of new ruthenium organometallic complexes derived from pyridine-imine ligands and their catalytic activity in oxidation of secondary alcohols

Reactions of pyridine imines [C5H4N-2-C(H)?=?N-C6H4-R] [R?=?H (1), CH3 (2), OMe (3), CF3 (4), Cl (5), Br (6)] with Ru3(CO)12 in refluxing toluene gave the corresponding dinuclear ruthenium carbonyl complexes of the type {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) [R?=?H (7); CH3 (8); OMe (9); CF3 (10); Cl (11); Br (12)]. All six novel complexes were separated by chromatography, and fully characterized by elemental analysis, IR, NMR spectroscopy. Molecular structures of 7, 10, 11, and 12 were determined by X-ray crystal diffraction. Further, the catalytic performance of these complexes was also tested. The combination of {μ-η2-CH[(2-C5H4N)(N-C6H4-R)]}2Ru2(CO)4(μ-CO) and NMO afforded an efficient catalytic system for the oxidation of a variety secondary alcohols.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Radical-mediated aerobic oxidation of substituted styrenes and stilbenes

A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.