109466-88-8

Basic information

• Product Name: 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE
• Synonyms: 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE
• CAS NO: 109466-88-8
• Molecular Formula: C₈H₆F₃NO
• Molecular Weight: 189.13
• Mol File: 109466-88-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE(109466-88-8)
• EPA Substance Registry System: 2-AMINO-4-(TRIFLUOROMETHYL)BENZALDEHYDE(109466-88-8)

Safety Data

• Hazardous Substances Data: 109466-88-8(Hazardous Substances Data)

Usage

Structure

Trifluoromethyl derivative of benzaldehyde with an amino group and a trifluoromethyl group attached to the benzene ring.

Common Uses

Building block in organic synthesis
Reagent in the synthesis of various heterocyclic compounds
Flavoring agent in the food industry

Applications

Pharmaceutical industry
Agrochemical industry
Materials science
Precursor to various fine chemicals

Upstream product

• 109134-07-8 t-butyl<3-(trifluoromethyl)phenyl>-carbamate 
• 68-12-2 N,N-dimethyl-formamide 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 186602-93-7 [2-amino-4-(trifluoromethyl)phenyl]methan-1-ol 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 98-16-8 3-trifluoromethylaniline 
• 109466-87-7 4-(trifluoromethyl)-2-nitrobenzaldehyde 
• 109466-86-6 4-(trifluoromethyl)-2-nitrobenzaldehyde oxime 

Downstream Products

• 324-32-3 2-methyl-7-trifluoromethylquinoline 
• 1395473-92-3 (S)-2-(4-methoxyphenyl)-7-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline 
• 1254343-12-8 (S)-2-phenyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroacridine 
• 849543-30-2 ethyl 7-(trifluoromethyl)-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 355399-88-1 [2-Oxo-6-phenyl-7-(trifluoromethyl)-1,2-dihydro-3-quinolyl]phosphonic acid diethyl ester 
• 355399-89-2 [(5-Trifluoromethyl-2-formyl-phenylcarbamoyl)-methyl]-phosphonic Acid Diethyl Ester 

Relevant articles and documents

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Cobalt in N-doped carbon matrix catalyst for chemoselective hydrogenation of nitroarenes

Anilines as important intermediates for both organic synthesis and industrial manufactory are densely substituted with a variety of functional moieties, and the transformation of nitroarenes into corresponding anilines requires catalytically selective hydrogenation catalyst. Herein, we describe a simple pyrolysis strategy to prepare cobalt catalysts in nitrogen-doped carbon matrix applied in the selective hydrogenation of nitroarenes with molecular hydrogen. The Co/NC catalysts are obtained through thermal treatment of mixed precursors of cobalt phthalocyanine and melamine. The surface-modified Co particles with Co3O4 and CoNx sites are surrounded by N-doped carbon layers according to a series of structural characterization results. These Co/NC catalysts are capable of efficiently selective hydrogenation of nitrobenzene and various substituted nitroarenes into corresponding anilines under relatively mild reaction conditions. The optimal catalytic hydrogenation performance is contributed to the fast rate of H2 dissociated activation on the CoNx active sites and the facile adsorption of the reactant substances, which is verified by the isotopic H2-D2 exchange experiments, reactant adsorption and the ORR reaction tests. Furthermore, the heterogeneous Co/NC catalyst is highly stable without the Co leaching and deactivation issues during the recycling reaction runs.

Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric C?C bonds

QUINOLIN-2-ONE DERIVATIVES

Compounds of the formula (I) in which X1, X2, X3, X4, R1, R2, R3, Q and Y have the meanings indicated in Claim 1, are inhibitors of c-Kit kinase, and can be employed for the treatment of cancer.

Versatile Barium and Calcium Imidazolium-Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

This article details the development of heterogeneous catalysts based on calcium and barium in combination with the organic linker 1,3-bis(carboxymethyl)imidazolium (bcmim). The linker and the materials from alkaline earth metals are easily prepared under very smooth conditions. The use of linkers with different counterions (Cl or Br) provided different materials. Calcium- and barium-based catalysts were successfully employed in the preparation of quinoline derivatives from ketones and 2-aminoarylaldehydes or 2-aminoarylketones. In general, barium-based catalysts provided better results than calcium, although the latter are an excellent complement for certain substrates. Thus, a notable feature of such catalysts is the possibility of accessing a variety of complementary heterogeneous catalytic systems, rendering the catalysis adaptive to the reactant.||||||.

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

Cyanoacetamides (IV): Versatile one-pot route to 2-quinoline-3-carboxamides

Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

HCV INHIBITORS AND METHODS OF USING THEM

The present invention comprises tetrazoloquinoline-compounds that are inhibitors of HCV. Compositions comprising the compounds in combination with a pharmaceutically acceptable carrier are also disclosed, as are methods of using the compounds and composit

Novel quinolinone-phosphonic acid AMPA antagonists devoid of nephrotoxicity.

We reported previously the synthesis and structure-activity relationships (SAR) in a series of 2-(1H)-oxoquinolines bearing different acidic functions in the 3-position. Exploiting these SAR, we were able to identify 6,7-dichloro-2-(1H)-oxoquinoline-3-phosphonic acid compound 3 (S 17625) as a potent, in vivo active AMPA antagonist. Unfortunately, during the course of the development, nephrotoxicity was manifest at therapeutically effective doses. Considering that some similitude exists between S 17625 and probenecid, a compound known to protect against the nephrotoxicity and/or slow the clearance of different drugs, we decided to synthesise some new analogues of S 17625 incorporating some of the salient features of probenecid. Replacement of the chlorine in position 6 by a sulfonylamine led to very potent AMPA antagonists endowed with good in vivo activity and lacking nephrotoxicity potential. Amongst the compounds evaluated, derivatives 7a and 7s appear to be the most promising and are currently evaluated in therapeutically relevant stroke models.

Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring a substituted camptothecin analogues. Structure-activity correlations

Nineteen racemic ring A substituted analogues of the antitumor agent 20(S)-camptothecin were prepared by total synthesis and evaluated for in vitro cytotoxic activity against KB cell culture and in vivo antileukemic activity against L1210. These compounds bore a wide variety of substitutents at C11 designed to confer upon the ring system a broad range of combinations of electronic, steric, and lipophilic effects. A few C10-substituted derivatives as well as C10,C11-disubstituted analogues prepared as part of a concurrent study have also been included for general comparison. With the notable exception of the cyano derivative, the 11-substituted compounds displayed only modest in vitro and in vivo activities, and there was a remarkable insensitivity toward the nature of the substituent. In contrast, the 9- and 10-substituted compounds exhibited a considerably higher level of dose potency and activity both in vitro and in vitro.