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

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

Used in Chemical Synthesis:
Methyl 3-hydroxythiophene-2-carboxylate is used as a reactant in synthesizing nitro-products, where it undergoes reactions with thiophenol. Its reactivity and functional groups make it a valuable intermediate in the production of various organic compounds and精细化工产品.
Used in Pharmaceutical Industry:
Methyl 3-hydroxythiophene-2-carboxylate is used in medicine, where its unique structure and properties can be leveraged for the development of pharmaceutical agents. Its potential applications may include the treatment of various diseases and conditions, as well as serving as a building block for the synthesis of more complex drug molecules.

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

Downstream Products

• 60166-83-8 3-methoxythiophene-2-carboxylic acid 
• 5118-07-0 3-hydroxythiophene-2-carboxylic acid 
• 139926-22-0 methyl 3-ethoxythiophene-2-carboxylate 
• 91041-19-9 3-(2-Chloro-6-nitro-phenoxy)-thiophene-2-carboxylic acid methyl ester 
• 91041-18-8 methyl 3-(2-nitrophenoxy)thiophene-2-carboxylate 
• 91041-20-2 3-(2-Nitro-4-trifluoromethyl-phenoxy)-thiophene-2-carboxylic acid methyl ester 
• 103790-37-0 methyl 3-(4-nitrophenoxy)thiophene-2-carboxylate 
• 104636-76-2 3-(2,4-Dinitro-phenoxy)-thiophene-2-carboxylic acid methyl ester 
• 91041-13-3 3-(4-Chloro-2-nitro-phenoxy)-thiophene-2-carboxylic acid methyl ester 
• 95201-93-7 methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate 
• 96232-71-2 4,5-dibromo-3-hydroxythiophene-2-carboxylic acid methyl ester 
• 144677-14-5 2-(1H-pyrazol-3-yl)acetohydrazide 
• 151824-93-0 3-Hydroxythiophen-2-carbohydroxamsaeure 
• 104386-71-2 methyl 3-hydroxy-5-phenylmercaptothiophene-2-carboxylate 

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.]

Imidazo [1, 2 - a] pyridine derivatives and preparation method and application thereof (by machine translation)

The invention discloses 3 -phenyl imidazo [1, 2 - a] pyridine derivatives represented by a formula (I) or 3 - (thiophene -2 substituted) imidazo [1, 2 - a] pyridine derivatives and a preparation method, and also discloses application. of the 3 -phenyimidazo [1, 2 - a] pyridine derivatives or 3 - (thiophene -2 substituted) imidazo [1, 2 - a] pyridine derivatives as a class of novel structural novel small molecule inhibitors, and the like. (by machine translation)

Preparation method of 3-hydroxythiophene-2-carboxylate compound

The invention provides a preparation method of a 3-hydroxythiophene-2-carboxylate compound. The preparation method comprises the following steps of enabling a formula as shown in the description to carry out a condensation reaction with E-3-methyl methoxyacrylate in an alkaline condition to form the 3-hydroxythiophene-2-carboxylate compound, wherein R is selected from any one of C1 to C10 alkyl and C2 to C10 alkenyl. The formula as shown in the description and the E-3-methyl methoxyacrylate are adopted as raw materials, and are enabled to carry out the condensation reaction in the alkaline condition to form a thiophene ring; the reaction is easy to carry out; the reaction condition is easy to control; and the product yield is higher in a proper condition. The cost of the E-3-methyl methoxyacrylate is lower compared with that of 2-methyl chloroacrylate or methyl propiolate; and therefore, the synthetic process cost of the 3-hydroxythiophene-2-carboxylate compound is decreased.

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.

3-alkoxy thiophene derivative and preparation method thereof

The invention provides a novel 3-alkoxy thiophene derivative and a preparation method thereof. The structure of the 3-alkoxy thiophene derivative is as shown in a chemical formula 1. The preparation method comprises the following steps that 1, a compound of a chemical formula 2 reacts with a compound of a chemical formula 3 to obtain a reaction product, the reaction product is subjected to hydrolysis, and a compound of a chemical formula 4 is obtained; 2, the obtained compound of the chemical formula 4 is subjected to a mono-alkylation reaction in a solvent, and a compound of a chemical formula 5 is obtained; 3, the obtained compound of the chemical formula 5 is heated to 80 DEG C to 300 DEG C under the condition of being free of solvent for a decarboxylation reaction; in the chemical formulas, R1 and R2 each independently adopts an alkyl group, and X adopts a halogen. The preparation method has the advantage of being capable of efficiently preparing the 3-alkoxy thiophene derivative in high yield.

3-Alkoxy-4-bromothiophenes: General synthesis of monomers and regio-selective preparation of two dimers

3-Alkoxy-4-bromothiophenes were synthesized in three steps from the readily available methyl 2-carboxylate-3-hydroxythiophene and two isomers of bithiophenes based on the 3-bromo-4-methoxythiophene moiety were regio-selectively prepared.

DNA-BINDING POLYMERS

Methods and compositions are provided for forming complexes between dsDNA and novel DNA-binding polymers comprising N-terminal thiophene-containing moieties which exhibit selectivity for T-A base pairs. By appropriate choice of target sequences and DNA-binding polymers, complexes comprising polymer-DNA are obtained with high association constants. The formation of complexes can be used for identification of specific dsDNA sequences, for inhibiting gene transcription, and as a therapeutic for inhibiting proliferation of undesired cells or modulation of expression of specific genes.

DNA-binding polymers

Methods and compositions are provided for forming complexes between dsDNA and novel DNA-binding polymers comprising N-terminal thiophene-containing moieties which exhibit selectivity for T-A base pairs. By appropriate choice of target sequences and DNA-binding polymers, complexes comprising polymer-DNA are obtained with high association constants. The formation of complexes can be used for identification of specific dsDNA sequences, for inhibiting gene transcription, and as a therapeutic for inhibiting proliferation of undesired cells or modulation of expression of specific genes.

CB1-MODULATING COMPOUNDS AND THEIR USE

Disclosed herein is a compound of Formula (I). Also disclosed herein is a method of modulating the activity of a cannabinoid receptor using a compound of Formula (I). Furthermore, disclosed herein is a method of treating a disease or condition that would