100501-60-8

Basic information

• Product Name: [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester
• Synonyms: [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester;2-[(2,3,4-Trifluoroanilino)methylene]malonic acid diethyl ester;2-[[(2,3,4-trifluorophenyl)amino]methylene]malonic acid diethyl ester;2-[[(2,3,4-trifluorophenyl)amino]methylene]propanedioic acid diethyl ester;BIM-0034963.P001;CBMicro_035050;diethyl 2-[[(2,3,4-trifluorophenyl)amino]methylene]propanedioate;diethyl 2-[[(2,3,4-trifluorophenyl)amino]methylidene]propanedioate
• CAS NO: 100501-60-8
• Molecular Formula: C₁₄H₁₄F₃NO₄
• Molecular Weight: 317.27
• Mol File: 100501-60-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester(100501-60-8)
• EPA Substance Registry System: [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester(100501-60-8)

Safety Data

• Hazardous Substances Data: 100501-60-8(Hazardous Substances Data)

Usage

Description

[[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is an organic compound characterized by its complex structure, which includes a trifluorophenyl group, an amino group, and a propanedioic acid diethyl ester group. [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is known for its unique chemical properties that make it a valuable component in the synthesis of various products.

Uses

Used in Pharmaceutical Synthesis:
[[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is used as a key intermediate in the synthesis of pharmaceuticals for its unique reactivity and structural properties. It contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, [[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is utilized as a building block for the creation of novel compounds with pesticidal, herbicidal, or fungicidal properties, aiming to enhance crop protection and yield.
Used in Specialty Chemicals:
[[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is employed as a versatile component in the synthesis of specialty chemicals, which are tailored for specific applications in various industries, such as coatings, adhesives, and materials science.
Used in Research and Development:
[[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester is also used as a research tool in academic and industrial laboratories to study its chemical behavior, reactivity, and potential applications in the development of new materials and chemical processes.

Upstream product

• 3862-73-5 2,3,4-trifluoroaniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 79660-46-1 ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 100501-62-0 ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 1262136-22-0 7-(4-benzylpiperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1262136-23-1 1-ethyl-6,8-difluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-48-9 6,8-difluoro-7-morpholino-4-oxo-1-(4-(trifluoromethyl) benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-52-5 6,8-difluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-53-6 7-(4-benzylpiperazin-1-yl)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-56-9 7-(butylamino)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-54-7 6,8-difluoro-7-(2-morpholinoethylamino)-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-55-8 6,8-difluoro-7-(3-morpholinopropylamino)-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-69-4 7-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)piperazin-1-yl)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-70-7 7-(4-(4,6-di(piperidin-1-yl)-1,3,5-triazin-2-yl)piperazin-1-yl)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-71-8 7-(4-(4,6-bis(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)piperazin-1-yl)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1293992-72-9 7-(4-(4,6-bis(2-morpholinoethylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

Thermochemical reaction of 7-azido-1-ethyl-6,8-difluoroquinolone-3-carboxylate with heterocyclic amines. An?expeditious synthesis of novel fluoroquinolone derivatives

Novel 7-hydrazino-1-ethyl-6,8-difluoroquinolone-3-carboxylate derivatives are obtained by thermochemical reaction of 7-azido-1-ethyl-6,8-difluoroquinolone-3-carboxylate with heterocyclic amines. These new fluoroquinolone carboxylates could be used as precursors in the preparation of novel fluoroquinolone carboxylic acids. These latter compounds are known to have biological activity.

Fluorine walk: The impact of fluorine in quinolone amides on their activity against African sleeping sickness

Human African Trypanosomiasis, also known as African sleeping sickness, is caused by the parasitic protozoa of the genus Trypanosoma. If there is no pharmacological intervention, the parasites can cross the blood-brain barrier (BBB), inevitably leading to death of the patients. Previous investigation identified the quinolone amide GHQ168 as a promising lead compound having a nanomolar activity against T. b. brucei. Here, the role of a fluorine substitution at different positions was investigated in regard to toxicity, pharmacokinetics, and antitrypanosomal activity. This ‘fluorine walk’ led to new compounds with improved metabolic stability and consistent activity against T. b. brucei. The ability of the new quinolone amides to cross the BBB was confirmed using an 18F-labelled quinolone amide derivative by means of ex vivo autoradiography of a murine brain.

Photochemistry of some non zwitterionic fluoroquinolones

Two non zwitterionic analogues of fluoroquinolone drugs, viz. 1-ethyl-7-piperidino-8-fluoroquinol-4- one-3-carboxylic acid and 1-ethyl-7-piperidino-6,8-difluoroquinol-4-one-3-carboxylic acids have been synthesized and their photochemistry has been investigated. Both compound undergo photoheterolysis of the C8 F bond generating a triplet cation that either inserts into the 1-alkyl chain or is trapped or reduced by external nucleophiles. The reaction is analogous to that observed with the corresponding (zwitterionic) 7-piperazino derivatives, but the quantum yield is ca five times lower. This supports the rationalization that in the latter case assistance to defluorination by the N+ H bond has a determining role.

Synthesis and in vitro antimicrobial evaluation of novel fluoroquinolone derivatives

A series of 1-ethyl-6,8-difluoro-4-oxo-7(4-aryl piperazin-1-yl) 1,4-dihydro-quinoline-3-carboxylic acid derivatives (6a-f) and 1-ethyl-6,8-difluoro-4-oxo-7(4-piperidin-1-yl) 1,4-dihydro-quinoline-3- carboxylic acid derivatives (7a-e) were synthesized and evaluated for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by the microbroth dilution technique. The compounds were also evaluated for antifungal activity against Candida albicans (ATCC 90028) and Cryptococcous neoformans (ATCC 14116) pathogens. The preliminary in vitro evaluation studies revealed that some of the compounds have promising antimicrobial activities.