5118-06-9

Basic information

• Product Name: Methyl 3-hydroxythiophene-2-carboxylate
• Synonyms: METHYL 3-HYDROXYTHIOPHENE-2-CARBOXYLATE;METHYL-3-HYDROXYTHIOPHENE CARBOXYLATE;METHYL 3-HYDROXY-2-THIOPHENECARBOXYLATE;3-HYDROXYTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;Methyl 3-hydroxythiophene-2-carboxylate ,97%;3-hydro-2-thiophenca;3-Hydroxy-2-(methoxycarbonyl)thiophene;3-Hydroxy-2-thiophenecarboxylic acid Methyl ester
• CAS NO: 5118-06-9
• Molecular Formula: C₆H₆O₃S
• Molecular Weight: 158.18
• EINECS: 1533716-785-6
• Product Categories: Esters;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 5118-06-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 38-43 °C(lit.)
• Boiling Point: 107-109°C 13mm
• Flash Point: >230 °F
• Appearance: white to light yellow crystal powder
• Density: 1.373 g/cm³
• Vapor Pressure: 0.039mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.47±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Methyl 3-hydroxythiophene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-hydroxythiophene-2-carboxylate(5118-06-9)
• EPA Substance Registry System: Methyl 3-hydroxythiophene-2-carboxylate(5118-06-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5118-06-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5118-06-9 differently. You can refer to the following data:
1. 3-Hydroxy-2-thiophenecarboxylic Acid Methyl Ester, is used as a reactant in synthesizing nitro-products where reaction occurs with thiophenol.
2. Methyl 3-hydroxythiophene-2-carboxylate is used in medicine.

Chemical Properties

white to light yellow crystal powder

Synthesis Reference(s)

Synthetic Communications, 9, p. 731, 1979 DOI: 10.1080/00397917908064186

InChI:InChI=1/C6H6O3S/c1-9-6(8)5-4(7)2-3-10-5/h2-3,7H,1H3

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 922-67-8 propynoic acid methyl ester 
• 80-63-7 methyl 2-chloroacrylate 
• 623-47-2 propynoic acid ethyl ester 
• 687-46-7 ethyl 2-chloroacrylate 
• 72721-02-9 5,6-dimethoxybenzimidazole 
• 95201-94-8 methyl 2-chloro-3-oxo-2,3-dihydrothiophen-2-yl-carboxylate 
• 5788-17-0 methyl (2E)-3-methoxy-2-propenoate 
• 3674-09-7 methyl 2,3-dichloropropionate 
• 2689-69-2 2-carbomethoxy-3-oxo tetrahydrothiophene 

Downstream Products

• 60166-83-8 3-methoxythiophene-2-carboxylic acid 
• 5118-07-0 3-hydroxythiophene-2-carboxylic acid 
• 186588-84-1 methyl 3-(benzyloxy)thiophene-2-carboxylate 
• 155330-74-8 C₂₃H₂₅NO₈S₃ 
• 155330-73-7 C₁₈H₂₂O₈S₂ 
• 89380-76-7 methyl 3-hydroxy-4-nitrothiothiophene-2-carboxylate 
• 89380-77-8 methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate 
• 62353-75-7 methyl 3-methoxy-2-thiophenecarboxylate 
• 186588-88-5 3-(benzyloxy)thiophene-2-carboxylic acid 
• 186588-86-3 Benzyl 3-(3-benzyloxythiophen-2-yl)-3-oxopropionate 

Relevant articles and documents

Design, synthesis, and structure activity relationship (SAR) studies of novel imidazo[1,2-a] pyridine derivatives as Nek2 inhibitors

Never in mitosis (NIMA) related kinase 2 (Nek2) is involved in multiple cellular processes such as cell cycle checkpoint regulation, cell division, DNA damage response and cell apoptosis. Nek2 has been reported to be overexpressed in various tumors and correlated with poor prognosis. Herein, a series of imidazo[1,2-a] pyridines Nek2 inhibitors were designed, synthesized, and their biological activities were investigated. Besides, structure activity relationship analysis of these compounds were performed in the MGC-803 cell. The screening results are promising, and compound 28e shows good proliferation inhibitory activity with an IC50 of 38 nM. The results would be helpful to design and develop more effective Nek2 inhibitors for the treatment of gastric cancer.

Identification of protein kinase fibroblast growth factor receptor 1 (FGFR1) inhibitors among the derivatives of 5-(5,6-dimethoxybenzimidazol-1-yl)-3-hydroxythiophene-2-carboxylic acid

Abstract: Fibroblast growth factor receptor 1 (FGFR1) plays an important role in tumorigenesis, suggesting that inhibitors of this protein kinase may become important compounds for the development of anticancer agents. Using molecular docking approach, we have identified a novel class of FGFR1 inhibitors belonging to the derivatives of 5-(5,6-dimethoxybenzimidazol-1-yl)-3-hydroxythiophene-2-carboxylic acid. It was revealed that the most promising compound 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[2-(methanesulfonyl)benzyloxy]thiophene-2-carboxylic acid methyl ester inhibits FGFR1 with an IC50 value of 150?nM in in vitro kinase assay. The structure–activity relationships have been studied, and the binding mode of this chemical class has been proposed. Graphic abstract: [Figure not available: see fulltext.]

SMALL MOLECULE INHIBITORS OF NEK2 AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having an imidazole pyrimidine structure which function as inhibitors of NEK2 protein, and their use as therapeutics for the treatment of cancer and other diseases.