154598-53-5

Basic information

• Product Name: 1-(2-AMINO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE
• Synonyms: 1-(2-AMINO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE;Ethanone, 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoro-;2-Trifluoroacetyl-4-chlorophenylaminehydrochloride;1-(2-AMNO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE;2-TRIFLUOROACETYL-4-CHLOROPHENYLAMINE HCL;1-(2-amino-5-chloro-3-methoxyphenyl)-2,2,2-trifluoro Ethanone;4-Chloro-2-(trifluoroacetyl)aniline, 1-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one;1-(2-aMino-4-chlorophenyl)-2,2,2-trifluoroethanone
• CAS NO: 154598-53-5
• Molecular Formula: C₈H₅ClF₃NO
• Molecular Weight: 223.5796096
• EINECS: 1806241-263-5
• Product Categories: Chemical Amines;Amines;Aromatics
• Mol File: 154598-53-5.mol

Chemical Properties

• Melting Point: 95-97°C
• Boiling Point: 282.279 °C at 760 mmHg
• Flash Point: 124.518 °C
• Appearance: Yellow solid
• Density: 1.475 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: -20?C Freezer
• PKA: -0.92±0.10(Predicted)
• CAS DataBase Reference: 1-(2-AMINO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-AMINO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE(154598-53-5)
• EPA Substance Registry System: 1-(2-AMINO-5-CHLOROPHENYL)-2,2,2-TRIFLUOROETHANONE(154598-53-5)

Safety Data

• Hazardous Substances Data: 154598-53-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C8H5ClF3NO/c9-4-1-2-6(13)5(3-4)7(14)8(10,11)12/h1-3H,13H2

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 
• 181190-33-0 N-(4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)pivalamide 
• 321-31-3 1-(3-chlorophenyl)-2,2,2-trifluoroethanone 
• 106-47-8 4-chloro-aniline 
• 541-73-1 1,3-Dichlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 886371-22-8 1-(2,5-dichloro-phenyl)-2,2,2-trifluoroethanone 
• 106-46-7 para-dichlorobenzene 
• 635-21-2 5-chloroanthranilic acid 
• 7033-50-3 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 173676-59-0 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone hydrochloride 

Downstream Products

• 173676-54-5 1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one 
• 927812-33-7 (αR)-2-amino-5-chloro-α-(2-cyclopropylethynyl)-α-(trifluoromethyl)benzenemethanol 
• 209414-27-7 (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 
• 168834-43-3 6-amino-3-chloro-α-cyclopropylethynyl-α-(trifluoromethyl)benzyl alcohol 
• 391860-73-4 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 168834-41-1 2-(2'-amino-5'-chlorophenyl)-1,1,1-trifluoro-4-phenylbut-3-yn-2-ol 
• 902772-07-0 ethyl 2-((4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)amino)-2-oxoacetate 
• 1262030-16-9 (1S,4R)-N-(4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide 
• 1262030-23-8 N,N-bis((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)-4-chloro-2-(2,2,2-trifluoroacetyl)aniline 
• 177530-94-8 (S)-N-(4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)pivalamide 
• 181190-33-0 N-(4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)pivalamide 
• 177530-95-9 (R)-N-(4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)pivalamide 
• 1453095-77-6 3,6-dichloro-2-cyclopropyl-4-(trifluoromethyl)quinoline 
• 1453095-78-7 3,6-dichloro-2-phenyl-4-(trifluoromethyl)quinoline 

Relevant articles and documents

α-(Trifluoromethyl)ethenyl boronic acid as a useful trifluoromethyl containing building block. Preparation and palladium-catalysed coupling with aryl halides

α-(Trifluoromethyl)ethenyl boronic acid was conveniently prepared from the reaction of readily available 2-bromotrifluoropropene with alkyl borate and magnesium in one-pot. This boronic acid can undergo palladium-catalysed coupling reactions with aryl halides to afford a series of useful α-(trifluoromethyl)styrene derivatives in high yield.

Benzylidene succinimides as 3C synthons for the asymmetric tandem Mannich reaction/transamidation of cyclic trifluoromethyl ketimines to obtain F3C-containing polycyclic dihydroquinazolinones

By taking advantage of benzylidene succinimides as a new class of 3C synthons, a highly diastereo- and enantioselective tandem Mannich reaction/transamidation has been established by reacting them with cyclic trifluoromethylN-acyl ketimines. Using aCinchonaalkaloid-derived squaramide as the catalyst, the tandem reaction proceeded smoothly under mild conditions and afforded a range of F3C-containing chiral polycyclic dihydroquinazolinones with excellent results (up to 99% yield, all cases >20?:?1 dr, up to 99% ee).

An entry to 2-(cyclobut-1-en-1-yl)-1: H -indoles through a cyclobutenylation/deprotection cascade

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles. Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism.

Method for synthesizing 4-chloro-2-(trifluoroacetyl) aniline by using micro-channel reactor

The invention belongs to the technical field of organic synthesis application, and provides a method for synthesizing 4-chloro-2-(trifluoroacetyl) aniline by using a micro-channel reactor. The methodcomprises the following steps of: respectively and synchronously adding a 2, 2, 2-trifluoro-(3'-chlorphenyl) ethanone solution, fuming sulfuric acid and fuming nitric acid into a first micro-channel reactor through a metering pump, and heating for nitration reaction to obtain 4-chloro-2- (trifluoroacetyl) nitrobenzene; and respectively adding a solution of 4-chloro-2- (trifluoroacetyl) nitrobenzene and hydrogen into a micro-mixer through a high-pressure constant-flow pump and a gas flow meter to finish gas-liquid two-phase mixing so as to obtain a gas-liquid mixture, adding the gas-liquid mixture into a second micro-channel reactor of which the inner wall is loaded with a catalyst, and heating for hydrogenation reaction to obtain the 4-chloro-2-(trifluoroacetyl) aniline. The target productobtained by the method for synthesizing the 4-chloro-2-(trifluoroacetyl) aniline by utilizing the micro-channel reactor provided by the invention is high in purity, stable in temperature control, safe in process and suitable for industrial popularization.

Construction of CF3-containing tetrahydropyrano[3,2- b]indoles through DMAP-catalyzed [4+1]/[3+3] domino sequential annulation

A [4+1]/[3+3] domino sequential annulation reaction of o-aminotrifluoroacetophenone derivatives and β′-acetoxy allenoates enabled by DMAP has been reported. A variety of CF3-containing tetrahydropyrano[3,2-b]indoles were obtained as a single diastereomer in high yields (≤98%) under mild conditions. The reaction can build one C-N bond, one C-C bond, and one C-O bond sequentially in a single step. The synthetic utility was demonstrated with gram-scale reactions and various transformations of the products.

Preparation method of 3',5'-dichloro-2,2,2-trifluoroacetophenone

The invention relates to the technical field of chemical pharmacy, particularly to a preparation method of 3',5'-dichloro-2,2,2-trifluoroacetophenone. According to the invention, 3',5'-dichloro-2,2,2-trifluoroacetophenone is prepared from 3'-chloro-2,2,2-trifluoroacetophenone as a raw material through four steps of nitrification, reduction, chlorination and deamination, and the method has the advantages of low raw material cost, mild reaction conditions, simple reaction process, facilitation of the reduction of the production cost, and improvement of the economic effect.

Synthetic method of efavirenz key intermediate

The invention provides a synthetic method of an efavirenz key intermediate. The synthetic method comprises the following steps: carrying out reaction on parachloroaniline and pivaloyl chloride to protect amino to obtain N-(4-chlorphenyl)-2,2-dimethyl propanamide; carrying out Friedel-Crafts acylation reaction on the product and Friedel-Crafts acylation under action of aluminum trichloride to hydrolyze to obtain 4-chloro-2-trifluoroacetyl aniline hydrochloride in an acidic condition; and then carrying out alkalization to obtain 4-chloro-2-trifluoroacetyl aniline, carrying out reaction with cyclopropyl acetylene magnesium chloride in a catalytic system formed by a ligand (1R, 2S)-1-phenyl-2-(1-pyrrolidyl)-1-propyl alcohol, and carrying out an asymmetrical self-catalytic reaction to obtain the efavirenz key intermediate. The synthetic method of the efavirenz key intermediate, provided by the invention, is cheap and easily available in raw material, low in toxicity of reagent and mild in reaction condition, amino protection and deprotection are not carried out frequently, the line is concise, the yields of reaction of each step are excellent, and the total yield is high.

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO-heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N-C and C-C bonds in one batch. A series of indolo[3, 2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N-C bond formation is followed by the C-C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N-C bond is formed. The resulting intermediate then cyclizes to make the C-C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration.

Method for preparing 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate and free alkalis thereof

The invention discloses a method for preparing a 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate and free alkalis thereof. The method comprises the steps: (1) subjecting an intermediate, which is obtained through subjecting a compound with a structure represented by a formula IV shown in the description to a reaction, to a reaction with trifluoroacetate or a compound with a structure represented by a formula V or a formula VI shown in the description, and then, carrying out acid treatment, so as to obtain a compound with a structure represented by a formula I shown in the description; (2) subjecting the compound with the structure represented by the formula I to a nitration reaction under the catalysis of an acid, so as to obtain a compound with a structure represented by a formula II shown in the description; and (3) subjecting the compound with the structure represented by the formula II to nitro-to-amino reduction, thereby obtaining a compound with a structure represented by a formula III shown in the description.

Palladium-catalyzed Suzuki–Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes

A mild and efficient palladium-catalyzed cross-coupling between fluorinated vinyl chloride and arylboronic acids is described. The use of ligand B successfully overcomes the strong electronic withdrawing of trifluoromethylated substrates and allows the efficient synthesis of a wide range of α and α,β-trifluoromethyl containing olefins. By using this method, the key intermediate for synthesis of Efavirenz can be obtained in a simple route. The efficient conversion of two freon molecules into useful α and α,β-trifluoromethyl containing olefins is a useful route in organic chemistry.