4651-81-4

Basic information

• Product Name: Methyl 2-aminothiophene-3-carboxylate
• Synonyms: AKOS 90546;METHYL 2-AMINOTHIOPHENE-3-CARBOXYLATE;methyl 2-amino-3-thenoate;METHYL 2-AMINO-3-THIOPHENECARBOXYLATE;BUTTPARK 46\18-81;ART-CHEM-BB B014692;METHYL 2-AMINOTHIOPHENE-3-CARBOXYLAT&;2-Amino-3-thiophenecarboxylic acid methyl ester
• CAS NO: 4651-81-4
• Molecular Formula: C₆H₇NO₂S
• Molecular Weight: 157.19
• EINECS: 225-084-8
• Product Categories: Amino Acids and Derivatives;Heterocycles;Esters;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Thiophene;Thiophenes & Benzothiophenes;Pharmaceutical intermediate;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 4651-81-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 76-81 °C(lit.)
• Boiling Point: 259.451 °C at 760 mmHg
• Flash Point: 110.712 °C
• Appearance: white to light yellow crystal powder
• Density: 1.32 g/cm³
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.10±0.10(Predicted)
• CAS DataBase Reference: Methyl 2-aminothiophene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-aminothiophene-3-carboxylate(4651-81-4)
• EPA Substance Registry System: Methyl 2-aminothiophene-3-carboxylate(4651-81-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4651-81-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 4651-81-4 differently. You can refer to the following data:
1. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
2. Methyl 2-aminothiophene-3-carboxylate may be used to prepare 3-thiaisatoic anhydride via hydrolysis, followed by the reaction with phosgene.

InChI:InChI=1/C6H7NO2S/c1-9-6(8)4-2-3-10-5(4)7/h2-3H,7H2,1H3

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 105-34-0 methyl 2-cyanoacetate 
• 67-56-1 methanol 
• 56387-08-7 2-aminothiophene-3-carboxylic acid 
• 53982-98-2 2-cyano-but-2-enoic acid methyl ester 
• 75-07-0 acetaldehyde 

Downstream Products

• 18740-38-0 1H-thieno[2,3-d]pyrimidine-2,4-dione 
• 103979-54-0 1H,2H,4H-thieno[2,3-d][1,3]oxazine-2,4-dione 
• 71309-26-7 2-[(phenylacetyl)amino]-thiophene-3-carboxylic acid methyl ester 
• 468096-17-5 methyl 2-({[(4-methylphenyl)amino]carbonothioyl}amino)thiophene-3-carboxylate 
• 338777-30-3 methyl 2-[(anilinocarbonothioyl)amino]thiophene-3-carboxylate 
• 468096-16-4 methyl 2-({[(4-chlorophenyl)amino]carbonothioyl}amino)thiophene-3-carboxylate 
• 55654-21-2 methyl 2-formylaminothiophene-3-carboxylate 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 
• 103979-58-4 1-(2-Methylamino-thiophen-3-yl)-3-phenyl-propane-1,3-dione 
• 103979-60-8 1-(3,4-Dimethoxy-phenyl)-3-(2-methylamino-thiophen-3-yl)-propane-1,3-dione 
• 18740-44-8 thieno<2,3-d>pyrimidin-2,4(1H,3H)-dithione 
• 18740-39-1 2,4-dichlorothieno[2,3-d]pyrimidine 
• 859204-09-4 2-(isopropylamino)-thiophen-3-carboxylic acid methyl ester 
• 126637-07-8 methyl 2-isothiocyanato-thiophene-3-carboxylate 

Relevant articles and documents

Design, synthesis, molecular docking and cytotoxic activity of novel urea derivatives of 2-amino-3-carbomethoxythiophene

Abstract: An efficient feasible route for the one-pot synthesis of novel series of urea derivatives (2a–2j) from 2-amino-3-carbomethoxythiophene (1) via in situ isocyanate has been developed, and their corresponding anticancer activities were accomplished. The series of urea derivatives were characterized by using 1H, 13C nuclear magnetic resonance and mass spectroscopic analysis. The cytotoxic activities were evaluated against human cervical (HeLa) and human lung (NCI-H23) cancer cell lines. These studies revealed satisfactory activity for some of the compounds, which could potentially serve as lead compounds for drug discovery and development. Furthermore, molecular docking studies supported in identifying the potential binding sites between the urea derivatives and eukaryotic ribonucleotidereductase (RR). High ambiguity driven docking (HADDOCK) modelling was specifically employed to determine the model complex of RR and urea derivatives. The proposed model has provided a deep insight into the molecular level interactions of RR-urea model complexes in understanding the exact pharmacophore for designing highly potent RR inhibitors. Overall, the present work has shed light in developing a feasible and robust approach for the synthesis of novel urea derivatives of 2-amino-3-carbomethoxythiophene and identified a part of molecular structure that is responsible for a specific biological interaction leading to potential anticancer activities. Graphic abstract: We report herein, the experimental design, synthesis and characterization of a novel series of urea derivatives of 2-amino-3carbomethoxythiophene with pyrimidine amine and benzyl amine analogues as both derivatives which exhibited potential antitumor activity via one pot synthesis and subsequently studied the structure activity relationships (SAR), and anticancer activities. The docking studies identified a part of molecularstructure that is responsible for a specific biological interaction leading to the destruction of cancer cells.[Figure not available: see fulltext.]

Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease

A set of CB2R ligands, based on the thiophene scaffold, was synthesized and evaluated in in vitro assays. Compounds 8c-i, k, l, bearing the 3-carboxylate and 2-(adamantan-1-yl)carboxamido groups together with apolar alkyl/aryl substituents at 5-position or at 4- and 5-positions of the thiophene ring possess high CB2R affinity at low nanomolar concentration, good receptor selectivity, and agonistic functional activity. The full agonist 8g, showing the best balance between receptor affinity and selectivity, was tested in vitro in an experimental model of allergic contact dermatitis and proved to be able to block the release of MCP-2 in HaCaT cells at 10 μM concentration.

New Thiophene Compound or Pharmaceutically Acceptable Salt Thereof Having Activation on PPAR, FXR and AMPK, and Medical Use Thereof

The present invention relates to a novel thiophene compound having activation on PPAR, FXR and AMPK or to a pharmaceutical composition or health functional food comprising a pharmaceutically acceptable salt thereof, wherein the compound can activate any one of PPAR sub types composed of andalpha;,andbeta; and andgamma;, and has an activation effect on FXR or AMPK, thereby being usefully used as the pharmaceutical composition for preventing or treating fatty liver disease including lipid hepatitis, or as the health functional food composition for prevention or improvement of fatty liver disease.COPYRIGHT KIPO 2017