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

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

Uses

Used in Pharmaceutical Industry:
Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agricultural Industry:
In the agricultural sector, Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate is used as a building block for the synthesis of various agrochemicals. Its potential applications include the development of new pesticides, herbicides, and other crop protection agents.
Used in Antitumor Research:
Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate is used as a potential antitumor agent in research settings. Its biological activity has been studied, and it may offer new avenues for the development of cancer treatments.

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

• 960001-03-0 E-Methyl 5-(6-chloro-5-fluoro-1H-benzimidazol-1-yl)-3-{[(1R)-1-{2-chloro-3-hydroxyphenyl)ethyl]oxy}-2-thiophenecarboxylate 
• 959909-81-0 methyl 5-{[4-(1-methyl-1H-pyrazol-4-yl)-2-nitrophenyl]amino}-3-[(phenylmethyl)oxy]-2-thiophenecarboxylate 
• 960001-00-7 methyl 5-[(5-chloro-4-fluoro-2-nitrophenyl)amino]-3-[(phenylmethyl)oxy]-2-thiophenecarboxylate 
• 960001-01-8 methyl 5-(6-chloro-5-fluoro-1H-benzimidazol-1-yl)-3-[(phenylmethyl)oxy]-2-thiophenecarboxylate 
• 959999-86-1 methyl 5-((2-amino-4-bromo-phenyl)amino)-3-benzyloxy-2-thiophenecarboxylate 
• 929095-36-3 methyl 5-[(5-{[(2,2-dimethylpropanoyl)oxy]methyl}-2-nitrophenyl)amino]-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)thiophene-2-carboxylate 
• 929095-37-4 methyl 5-[(2-amino-5-{[(2,2-dimethylpropanoyl)oxy]methyl}phenyl)amino]-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)thiophene-2-carboxylate 
• 929278-62-6 methyl 5-[(4-bromo-2-nitrophenyl)amino]-3-[(phenylmethyl)oxy]-2-thiophenecarboxylate 
• 929039-92-9 methyl 5-amino-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate 
• 929095-38-5 methyl 5-(6-{[(2,2-dimethylpropanoyl)oxy]methyl}-1H-benzimidazol-1-yl)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)thiophene-2-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.

Synthesis of functionalized hydroxy-thiophene motifs as amido- and sulfonamido-phenol bioisosteres

Novel highly substituted hydroxy thiophene motifs were designed and synthesized as viable amido phenol and sulfonamido phenol bioisosteres. Hydroxy group-directed regioselective bromination and palladium-catalyzed amination of thienyl bromide via Buckwald

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.