78267-15-9

Basic information

• Product Name: ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE
• Synonyms: ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE;3-thiophenecarboxylic acid, 4,5-dihydro-4-oxo-2-(phenylami;ethyl 2-anilino-4-oxo-4,5-dihydrothiophene-3-carboxylate;4-keto-2-(phenylamino)thiophene-3-carboxylic acid ethyl ester;4-oxo-2-(phenylamino)-3-thiophenecarboxylic acid ethyl ester;ethyl 4-oxo-2-(phenylamino)thiophene-3-carboxylate;ethyl 2-anilino-4-oxo-thiophene-3-carboxylate
• CAS NO: 78267-15-9
• Molecular Formula: C₁₃H₁₃NO₃S
• Molecular Weight: 263.31
• Mol File: 78267-15-9.mol

Chemical Properties

• Melting Point: 147-149°C
• Boiling Point: 402.2°C at 760 mmHg
• Flash Point: 197°C
• Appearance: /
• Density: 1.364g/cm³
• Vapor Pressure: 1.12E-06mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C(protect from light)
• PKA: -2.54±0.20(Predicted)
• CAS DataBase Reference: ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE(78267-15-9)
• EPA Substance Registry System: ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE(78267-15-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 78267-15-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs. Its complex molecular structure allows for the creation of compounds with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE serves as a building block in the formulation of agrochemicals, potentially enhancing crop protection and yield through its incorporation into pesticides, herbicides, or other agricultural products.
Used in Organic Synthesis:
ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE is utilized as a versatile reagent in organic synthesis, enabling the creation of a diverse array of organic compounds for research and industrial applications.
Used in Biological Research:
Due to its potential biological activity, ETHYL 2-ANILINO-4-OXO-4,5-DIHYDRO-3-THIOPHENECARBOXYLATE is used in biological research to explore its interactions with biological systems, which may lead to the discovery of new therapeutic agents or insights into disease mechanisms.

InChI:InChI=1/C13H13NO3S/c1-2-17-13(16)11-10(15)8-18-12(11)14-9-6-4-3-5-7-9/h3-7,14H,2,8H2,1H3

Upstream product

• 62-53-3 aniline 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 78267-20-6 ethyl 2-anilino-5-p-chlorophenylhydrazono-4-oxo-4,5-dihydrothiophen-3-carboxylate 
• 78267-18-2 ethyl 2-anilino-5-methylbenzylidene-4-oxo-4,5-dihydrothiophen-3-carboxylate 
• 78267-19-3 ethyl 5-acetoxy-2-anilino-4-oxo-4,5-dihydrothiophen-3-carboxylate 
• 297159-77-4 ethyl (Z)-5-(4-methoxybenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate 
• 403713-98-4 ethyl (Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate 
• 78267-30-8 diethyl 2,2'-dianilino-4,4'-dichloro-5,5'-azinomethylbi(thiophenyl-3,3'-dicarboxylate) 
• 78267-35-3 ethyl 2-anilino-5-(5-anilino-4-ethoxycarbonyl-3-oxo-2,3-dihydro-2-thienylidenemethyl)-4-chlorothiophen-3-carboxylate 
• 78267-32-0 ethyl 2-anilino-4-chloro-5-(2,4-dinitrophenyl)hydrazonothiophen-3-carboxylate 
• 78267-28-4 ethyl 2-anilino-4-chloro-5-(p-chlorophenyliminomethyl)thiophen-3-carboxylate 
• 78267-37-5 diethyl (2-anilinothieno<3,2-b>thiophen)-3,5-dicarboxylate 
• 78267-31-9 ethyl 2-anilino-4-chloro-5-dimethylhydrazonothiophen-3-carboxylate 
• 78267-36-4 ethyl 2-anilino-5-formyl-4-(phenylthio)thiophen-3-carboxylate 
• 78267-33-1 ethyl 2-anilino-4-chloro-5-hydroxyiminothiophen-3-carboxylate 
• 78267-29-5 ethyl 2-anilino-4-chloro-5-hydrazonothiophen-3-carboxylate 

Relevant articles and documents

Novel selective and potent inhibitors of malaria parasite dihydroorotate dehydrogenase: Discovery and optimization of dihydrothiophenone derivatives

Taking the emergence of drug resistance and lack of effective antimalarial vaccines into consideration, it is of significant importance to develop novel antimalarial agents for the treatment of malaria. Herein, we elucidated the discovery and structure-activity relationships of a series of dihydrothiophenone derivatives as novel specific inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH). The most promising compound, 50, selectively inhibited PfDHODH (IC50 = 6 nM, with >14 000-fold species-selectivity over hDHODH) and parasite growth in vitro (IC50 = 15 and 18 nM against 3D7 and Dd2 cells, respectively). Moreover, an oral bioavailability of 40% for compound 50 was determined from in vivo pharmacokinetic studies. These results further indicate that PfDHODH is an effective target for antimalarial chemotherapy, and the novel scaffolds reported in this work might lead to the discovery of new antimalarial agents.

Synthesis of α-oxo-sulfines in the indole series

(Chemical Equation Presented) Oxindole was found to react readily with thionyl chloride to give (in an excellent yield) the isolable sulfine (13a), which on heating (refluxing acetonitrile) gave isoindigo (15a). The dark violet 3-sulfinatooxindole (13a) readily reacted with 2,3-dimethylbutadiene to give a colorless cyclo-adduct (14a). The sulfine also reacted readily with various nucleophilic reagents, thus, thioloacetic acid gave 3-carboxymethylthiolo- oxindole (23a).

Some Reactions of Ethyl 2-Anilino-4-oxo-4,5-dihydrothiophen-3-carboxylate

Phenyl isothiocyanate reacts with ethyl γ-chloroacetoacetate in the presence of sodium hydride to give ethyl 2-anilino-4-oxo-4,5-dihydrothiophen-3-carboxylate (1b).The compound (1b) shows typical reactions of a keto-methylene compound; the Vilsmeier reage