89380-77-8

Basic information

• Product Name: Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate
• Synonyms: 2-THIOPHENECARBOXYLIC ACID, 3-HYDROXY-5-NITRO-, METHYL ESTER;2-Thiophenecarboxylicacid,3-hydroxy-5-nitro-,methylester(7CI,9CI);METHYL 3-HYDROXY-5-NITRO-2-THIOPHENECARBOXYLATE;3-Hydroxy-5-nitrothiophene-2-carboxylic acid methyl ester;methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate:3-hydroxy-5-nitrothiophene-2-carboxylic acid methyl ester
• CAS NO: 89380-77-8
• Molecular Formula: C₆H₅NO₅S
• Molecular Weight: 203.17
• Product Categories: AMINOACID
• Mol File: 89380-77-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 329.379 °C at 760 mmHg
• Flash Point: 153.003 °C
• Appearance: /
• Density: 1.599 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate(89380-77-8)
• EPA Substance Registry System: Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate(89380-77-8)

Safety Data

• Hazardous Substances Data: 89380-77-8(Hazardous Substances Data)

Usage

General Description

Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate is an organic compound with a molecular formula C7H7NO5S. It is a member of the thiophene family, containing a thiophene ring with a nitro and hydroxy group attached to it. This chemical is commonly used in pharmaceutical and agricultural applications, particularly for its potential as a building block in the synthesis of various compounds. Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate may also exhibit biological activity and has been studied for its potential as an antitumor agent. However, it is important to handle this compound with care, as it may pose hazards to human health and the environment.

InChI:InChI=1/C6H5NO5S/c1-12-6(9)5-3(8)2-4(13-5)7(10)11/h2,8H,1H3

Upstream product

• 5118-06-9 methyl 3-hydroxy-2-thiophenecarboxylate 

Downstream Products

• 1276687-26-3 methyl (+/-)-5-nitro-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 929278-58-0 methyl 3-(benzyloxy)-5-nitrothiophene-2-carboxylate 
• 1276687-27-4 methyl (+/-)-5-amino-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 929278-60-4 methyl 5-amino-3-(benzyloxy)thiophene-2-carboxylate 
• 1276687-28-5 methyl (+/-)-5-(5-(4-methoxybenzyloxy)-2-nitrophenylamino)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 1276687-29-6 methyl 3-(benzyloxy)-5-(5-(4-methoxybenzyloxy)-2-nitrophenylamino)thiophene-2-carboxylate 
• 1276687-30-9 methyl 3-methoxy-5-(2-nitrophenylamino)thiophene-2-carboxylate 
• 1276687-31-0 methyl (+/-)-5-(2-nitrophenylamino)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 1276687-32-1 methyl (+/-)-5-(6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-1-yl)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 1276687-33-2 methyl 3-(benzyloxy)-5-(6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxylate 
• 1276687-35-4 methyl (+/-)-5-(1H-benzo[d]imidazol-1-yl)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 1276687-36-5 methyl (+/-)-5-(6-hydroxy-1H-benzo[d]imidazol-1-yl)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate 
• 1276687-37-6 methyl 3-(benzyloxy)-5-(6-hydroxy-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxylate 
• 1276687-38-7 tert-butyl (+/-)-4-(1-(5-(methoxycarbonyl)-4-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophen-2-yl)-1H-benzo[d]imidazol-6-yloxy)piperidine-1-carboxylate 

Relevant articles and documents

Benzimidazole inhibitors induce a DFG-out conformation of never in mitosis gene a-related kinase 2 (Nek2) without binding to the back pocket and reveal a nonlinear structure-activity relationship

We describe herein the structure-activity relationship (SAR) and cocrystal structures of a series of Nek2 inhibitors derived from the published polo-like kinase 1 (Plk1) inhibitor (R)-1. Our studies reveal a nonlinear SAR for Nek2 and our cocrystal structures show that compounds in this series bind to a DFG-out conformation of Nek2 without extending into the enlarged back pocket commonly found in this conformation. These observations were further investigated, and structure-based design led to Nek2 inhibitors derived from (R)-1 with more than a hundred-fold selectivity against Plk1.

Nitration of Methyl 3-Hydroxy- and 5-methyl-3-hydroxythipophene-2-carboxylate, and Some Chemistry of the Products

The nitration of methyl 3-hydroxythiophene-2-carboxylate furnishes two products, the lower melting of which was previously thought to be the 4-(3) and the other the 5-isomer (2); these assignments have been reversed on the basis of carbon-13 n.m.r. data. Further, the revised structures were confirmed both by O to N acyl migrations and by the preparation of the first examples (20) and (23) of the thieno[3,4-b][1,4]oxazine ring system from derivatives of the 4-nitro isomer.