205756-71-4

Basic information

• Product Name: Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro- (9CI)
• Synonyms: Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro- (9CI);2'-Amino-5'-methoxy-2,2,2-trifluoroacetophenone;4-Amino-3-(trifluoroacetyl)anisole,4-Methoxy-2-(trifluoroacetyl)aniline,1-(2-Amino-5-methoxyphenyl)-2,2,2-trifluoroethan-1-one;1-(2-Amino-5-methoxyphenyl)-2,2,2-trifluoroethanone
• CAS NO: 205756-71-4
• Molecular Formula: C₉H₈F₃NO₂
• Molecular Weight: 219.1605296
• Product Categories: ACETYLHALIDE
• Mol File: 205756-71-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro- (9CI)(205756-71-4)
• EPA Substance Registry System: Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro- (9CI)(205756-71-4)

Safety Data

• Hazardous Substances Data: 205756-71-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro(9CI) is utilized as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structural features and potential biological activity. Its presence of a trifluoromethyl group, an amino group, and a methoxy group attached to a phenyl ring allows for the development of new drugs with improved pharmacological properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro(9CI) serves as a building block for the design and synthesis of novel bioactive molecules. Its unique functional groups enable the creation of diverse chemical entities with potential therapeutic applications, such as antimicrobial, antiviral, and anticancer agents.
Used in Drug Discovery:
Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro(9CI) is employed as a starting material in drug discovery processes, where its structural modifications can lead to the development of new pharmaceutical agents with enhanced efficacy and selectivity. Its presence in compound libraries aids in high-throughput screening efforts to identify promising drug candidates for further optimization and development.
Used in Chemical Synthesis:
Beyond its applications in the pharmaceutical industry, Ethanone, 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro(9CI) also finds use in various chemical synthesis processes. Its unique functional groups make it a versatile building block for the preparation of a wide range of organic compounds, including agrochemicals, dyes, and specialty chemicals.

Upstream product

• 104-94-9 4-methoxy-aniline 
• 56619-94-4 4-methoxy-N-pivaloylaniline 

Downstream Products

• 1233967-23-1 1-(2-amino-5-hydroxyphenyl)-2,2,2-trifluoroethanone 
• 1456900-26-7 C₁₈H₁₄F₃NO 
• 1453095-80-1 3-chloro-6-methoxy-2-phenyl-4-(trifluoromethyl)quinoline 

Relevant articles and documents

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).

Trifluoromethyl-promoted homocamptothecins: Synthesis and biological activity

The homocamptothecin (hCPT) represents a new class of topoisomerase inhibitor which combines enhanced plasma stability and strong antitumor activity. Fluorine imparts desirable characteristics to drugs by modulating both the pharmacokinetics and pharmacodynamic properties of a drug. Therefore, in an attempt to improve the antitumor activity of homocamptothecins, seven new 7-trifluoromethylated homocamptothecin derivatives were prepared by proline-catalyzed Friedlander annulation. The antitumor activity in vitro and in vivo on cancer cell lines, and inhibitory properties of topoisomerase I-mediated DNA cleavage of compounds 6c and 8b were evaluated. Several of these trifluoromethylated hCPT derivatives (such as 6a, 6b and 6c) possessed higher in vitro antitumor activity than topotecan (TPT). Especially, the compound 6c showed effective in vivo antitumor activity comparable to that of TPT.

An alternative route for synthesis of o-trifluoroacetylanilines as useful fluorine-containing intermediates

A series of o-trifluoroacetyl aniline derivatives were synthesized in three steps. In this method, we first utilized trifluoroacetic anhydride to introduce trifluoroacetyl group to the ortho position of aniline with higher yield than that of some previously reported methods. In addition, the procedure is shown to be highly regiospecific. This type of compounds can be used as the key intermediates in the preparation of a variety of inhibitors of HIV reverse transcriptase which is an important pharmacological target of many anti-AIDS agents.

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.