205756-35-0

Basic information

• Product Name: Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro- (9CI)
• Synonyms: Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro- (9CI);1 - (2 - AMino - 5 - Methylphenyl) - 2,2,2 - trifluoroethanone;1-(2-Amino-5-methylphenyl)-2,2,2-trifluoroethan-1-one, 4-Methyl-2-(trifluoroacetyl)aniline;2'-Amino-5'-methyl-2,2,2-trifluoroacetophenone
• CAS NO: 205756-35-0
• Molecular Formula: C₉H₈F₃NO
• Molecular Weight: 203.1611296
• Product Categories: ACETYLHALIDE
• Mol File: 205756-35-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro- (9CI)(205756-35-0)
• EPA Substance Registry System: Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro- (9CI)(205756-35-0)

Safety Data

• Hazardous Substances Data: 205756-35-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro(9CI) serves as a key intermediate in the development of new drugs. Its trifluoromethyl group imparts unique properties that can improve the activity, selectivity, and pharmacokinetics of drug candidates, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro(9CI) is utilized as a building block for the synthesis of crop protection agents. Its chemical structure allows for the creation of novel compounds with enhanced pesticidal properties, contributing to more effective and targeted crop protection solutions.
Used in Organic Synthesis:
Ethanone, 1-(2-amino-5-methylphenyl)-2,2,2-trifluoro(9CI) is a versatile intermediate in organic synthesis, enabling the creation of a wide range of chemical compounds. Its unique structure and functional groups facilitate various chemical reactions, making it a valuable component in the synthesis of complex organic molecules for diverse applications.

Upstream product

• 205756-34-9 2,2-Dimethyl-N-[4-methyl-2-(2,2,2-trifluoro-acetyl)-phenyl]-propionamide 
• 29289-13-2 2-iodo-4-methylaniline 
• 205756-33-8 N-(2-iodo-4-methylphenyl)pivalamide 
• 106-49-0 p-toluidine 
• 21354-40-5 2,2-dimethyl-N-(4-methylphenyl)propanamide 

Downstream Products

• 1370794-47-0 (2S)-2-(2-amino-5-methylphenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 

Relevant articles and documents

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).

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.

Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition

A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).

NHC-Cu(I)-Catalyzed Friedl?nder-Type Annulation of Fluorinated o-Aminophenones with Alkynes on Water: Competitive Base-Catalyzed Dibenzo[b,f][1,5]diazocine Formation

An efficient, easily scalable synthesis of 4-trifluoromethylquinolines and naphthydrines (as well as their difluoro- and perfluoro-analogues) as a result of tandem direct catalytic alkynylation/dehydrative condensation of o-aminofluoromethylketones (o-FMKs), for the first time catalyzed by NHC-copper(I) complexes on water, is reported. A wide range of terminal alkynes is tolerated under the reaction conditions, including β-lactam-, steroid-, and sugar-derived ones, leading to desired quinolines and naphthydrines with good yields. Further investigations proved that o-FMKs could be efficiently transformed into a rare class of heterocyclic compounds - dibenzo[b,f][1,5]diazocines - by a base-catalyzed condensation, also on water. The developed method was applied for gram-scale synthesis of a fluorinated analogue of G protein-coupled receptor antagonist (GPR91).

Synthesis and evaluation of analogs of Efavirenz (SUSTIVA(TM)) as HIV-1 reverse transcriptase inhibitors

Efavirenz (SUSTIVA(TM)) is a potent non-nucleoside reverse transcriptase inhibitor. Due to the observation of breakthrough mutations of the reverse transcriptase enzyme during Efavirenz therapy, we sought to develop an optimized second generation series. To that end, SAR of the substituents on the aromatic ring was undertaken and the results are summarized here. The 5,6-difluoro (4f) and the 6-methoxy (4m) substituted benzoxazinones were determined to be equipotent, and as a result such substitution patterns will be incorporated in second generation scaffolds.

4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same

The present invention relates to benzoxazinones of formula I: STR1 or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.