5860-95-7

Basic information

• Product Name: 2'-Chloro-2,2,2-Trifluoroacetophenone
• Synonyms: Ethanone, 1-(2-chlorophenyl)-2,2,2-trifluoro-
• CAS NO: 5860-95-7
• Molecular Formula: C₈H₄ClF₃O
• Molecular Weight: 208.565
• Product Categories: Fluorine series
• Mol File: 5860-95-7.mol

Chemical Properties

• Melting Point: 77-80℃
• Boiling Point: 180℃
• Flash Point: 63℃
• Appearance: /
• Density: 1.396
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2'-Chloro-2,2,2-Trifluoroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Chloro-2,2,2-Trifluoroacetophenone(5860-95-7)
• EPA Substance Registry System: 2'-Chloro-2,2,2-Trifluoroacetophenone(5860-95-7)

Safety Data

• Hazardous Substances Data: 5860-95-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Chloro-2,2,2-Trifluoroacetophenone is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2'-Chloro-2,2,2-Trifluoroacetophenone is utilized as an intermediate in the production of agrochemicals, aiding in the creation of compounds that can protect crops and enhance agricultural productivity.
Used in Specialty Chemicals Production:
2'-Chloro-2,2,2-Trifluoroacetophenone is employed as a building block in the production of specialty chemicals, where its unique properties are leveraged to create high-value compounds for specific applications.
Used in Organic Chemistry as a Reagent:
2'-Chloro-2,2,2-Trifluoroacetophenone is used as a reagent in organic chemistry reactions, particularly for the synthesis of heterocyclic compounds, due to its reactive nature and ability to participate in various chemical transformations.

Upstream product

• 353-85-5 trifluoroacetonitrile 
• 694-80-4 2-bromo-1-chlorobenzene 
• 89-98-5 2-chloro-benzaldehyde 
• 75-46-7 trifluoromethan 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 610-96-8 methyl chlorobenzoate 
• 251352-64-4 1-(2-chlorophenyl)-2,2,2-trifluoroethanol 

Downstream Products

• 935265-34-2 1-(2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl)-2,2,2-trifluoroethanone 
• 1050445-66-3 2-(2-chlorophenyl)-1,1,1-trifluorobutan-2-ol 

Relevant articles and documents

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.

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.

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

High-Pressure-Mediated Asymmetric Organocatalytic Hydroxyalkylation of Indoles with Trifluoromethyl Ketones

An enantioselective hydroxyalkylation of indoles and 7-azaindole with trifluoromethyl ketones was found to be effectively promoted under high-pressure conditions with a low loading of Cinchona alkaloids (e.g., 1–3 mol% of cinchonidine). Chiral tertiary alcohols containing a trifluoromethyl group were obtained at 9 kbar with good yield and enantioselectivity up to 89%, whereas usually merely traces of products were detected at atmospheric pressure. (Figure presented.).

Synthesis of 3-fluoromethyl-2,1-benzisoxazoles

A convenient synthetic method to access hitherto unknown 3-(trifluoromethyl)- and 3-(difluoromethyl)-2,1-benzisoxazoles by the reaction of sodium azide with 1-(2-halophenyl)-2,2,2-trifluoroethanones or 1-(2-halophenyl)-2,2-difluoroethanones was developed. 3-Fluoromethyl-2,1-benzisoxazoles are versatile precursors for o-fluoroacetylanilines.

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K2CO3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o-iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and heteroaryl trifluoromethyl ketones.

A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation

Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation.