119004-72-7

Basic information

• Product Name: 2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: CHEMBRDG-BB 3000482;ART-CHEM-BB B000482;METHYL 2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE;AKOS B000482;2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER;methyl 2-amino-6-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate(SALTDATA: FREE);Methyl 2-aMino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate;methyl 2-amino-6-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-ca
• CAS NO: 119004-72-7
• Molecular Formula: C₁₆H₁₇NO₂S
• Molecular Weight: 287.38
• Mol File: 119004-72-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 472.6°C at 760 mmHg
• Flash Point: 239.6°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 4.22E-09mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(119004-72-7)
• EPA Substance Registry System: 2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(119004-72-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 119004-72-7(Hazardous Substances Data)

Usage

General Description

2-AMINO-6-PHENYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER is a chemical compound that belongs to the class of benzo[b]thiophene derivatives. It consists of a benzo[b]thiophene ring with a phenyl and amino group attached at the 6th and 2nd positions, respectively. The compound also contains a carboxylic acid and a methyl ester functional group. This chemical compound has potential pharmaceutical applications due to its structural features and could be used in the development of new drugs targeting various biological pathways. Additionally, it may also have industrial uses in the synthesis of other organic compounds.

InChI:InChI=1/C16H17NO2S/c1-19-16(18)14-12-8-7-11(9-13(12)20-15(14)17)10-5-3-2-4-6-10/h2-6,11H,7-9,17H2,1H3

Upstream product

• 4894-75-1 1-phenyl-4-cyclohexanone 
• 105-34-0 methyl 2-cyanoacetate 
• 10544-50-0 sulfur 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 1574665-10-3 2-[(tert-butoxycarbonyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1574665-18-1 N-isopropyl 2-[(tert-butoxycarbonyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574665-15-8 [2-((tert-butoxycarbonyl)amino)-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thien-3-yl]-4-morpholinylmethanone 
• 1574665-21-6 N-phenyl 2-[(tert-butoxycarbonyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574665-24-9 N-benzyl 2-[(tert-butoxycarbonyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574664-54-2 methyl 2-[(3-carbamoyl-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1574664-66-6 2-[(3-carboxy-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1574664-71-3 methyl 2-[(2-carboxy-1-oxomethyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1574664-79-1 N-isopropyl 2-[(3-carboxy-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574664-82-6 [2-[(3-carboxy-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thien-3-yl]-4-morpholinylmethanone 
• 1574664-86-0 N-phenyl 2-[(3-carboxy-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574664-88-2 N-benzyl 2-[(3-carboxy-1-oxopropyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 1574665-13-6 C₂₁H₂₅NO₄S 
• 357932-80-0 methyl 2-[[(6-carboxy-3-cyclohexen-1-yl)carbonyl]amino]-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 

Relevant articles and documents

Synthesis and biological evaluation of new antitubulin agents containing 2-(30,40,50-trimethoxyanilino)-3,6-disubstituted-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Scaffold

Two novel series of compounds based on the 4,5,6,7-tetrahydrothieno[2,3-c]pyridine and 4,5,6,7-tetrahydrobenzo[b]thiophene molecular skeleton, characterized by the presence of a 30,40,50-trimethoxyanilino moiety and a cyano or an alkoxycarbonyl group at its 2- or 3-position, respectively, were designed, synthesized, and evaluated for antiproliferative activity on a panel of cancer cell lines and for selected highly active compounds, inhibition of tubulin polymerization, and cell cycle effects. We have identified the 2-(30,40,50-trimethoxyanilino)-3-cyano-6-methoxycarbonyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivative 3a and its 6-ethoxycarbonyl homologue 3b as new antiproliferative agents that inhibit cancer cell growth with IC50 values ranging from 1.1 to 4.7 μM against a panel of three cancer cell lines. Their interaction with tubulin at micromolar levels leads to the accumulation of cells in the G2/M phase of the cell cycle and to an apoptotic cell death. The cell apoptosis study found that compounds 3a and 3b were very effective in the induction of apoptosis in a dose-dependent manner. These two derivatives did not induce cell death in normal human peripheral blood mononuclear cells, suggesting that they may be selective against cancer cells. Molecular docking studies confirmed that the inhibitory activity of these molecules on tubulin polymerization derived from binding to the colchicine site.

A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates

A simple method for the preparation of alkyl 2-aminobenzo[b]thiophene-3-carboxylates is described. Alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates, generated from the Gewald three-component reaction between cyclohexanones, alkyl cyanoacetates and sulfur, undergo dehydrogenation in benzonitrile under an air atmosphere to afford alkyl 2-aminobenzo[b]thiophene-3-carboxylates in good to excellent yields.

A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates

A simple method for the preparation of alkyl 2-aminobenzo[b]thiophene-3-carboxylates is described. Alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates, generated from the Gewald three-component reaction between cyclohexanones, alkyl cyanoacet