55341-87-2

Basic information

• Product Name: 3-Aminothiophene-2-carboxylic acid
• Synonyms: 2-Thiophenecarboxylicacid,3-amino-(6CI,9CI);3-AMINO-2-THIOPHENECARBOXYLIC ACID POTASSIUM SALT;3-amino-2-thenoic acid;potassium 3-aminothiophene-2-carboxylic acid
• CAS NO: 55341-87-2
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.17
• Product Categories: AMINOACID;pharmacetical;Heterocycles series
• Mol File: 55341-87-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 82 °C (decomp)
• Boiling Point: 399 °C at 760 mmHg
• Flash Point: 195.1 °C
• Appearance: /
• Density: 1.527 g/cm³
• Vapor Pressure: 4.4E-07mmHg at 25°C
• Refractive Index: 1.689
• PKA: 4.07±0.10(Predicted)
• CAS DataBase Reference: 3-Aminothiophene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminothiophene-2-carboxylic acid(55341-87-2)
• EPA Substance Registry System: 3-Aminothiophene-2-carboxylic acid(55341-87-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 55341-87-2(Hazardous Substances Data)

Usage

General Description

3-Aminothiophene-2-carboxylic acid is a chemical compound with the molecular formula C6H5NO2S. It is a yellow solid that is insoluble in water but soluble in organic solvents. 3-Aminothiophene-2-carboxylic acid is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential antitumor and antiviral properties. Additionally, 3-Aminothiophene-2-carboxylic acid is known to have a strong and characteristic odor. Overall, this compound has various industrial and medicinal applications due to its unique chemical properties and potential biological activity.

InChI:InChI=1/C5H5NO2S/c6-3-1-2-9-4(3)5(7)8/h1-2H,6H2,(H,7,8)

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 132221-25-1 [1-(4-Bromo-2-fluoro-benzyl)-2,4-dioxo-1,4-dihydro-2H-thieno[3,2-d]pyrimidin-3-yl]-acetic acid 
• 78756-28-2 2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione 
• 65076-02-0 ethyl 2-ethoxycarbonyl-3-(thienylamino)prop-2-enoate 
• 50901-18-3 3-acetamidothiophene-2-carboxylic acid 
• 194088-56-7 3-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-thiophene-2-carboxylic acid 
• 194088-58-9 3-[(S)-2-Benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-thiophene-2-carboxylic acid 
• 194088-59-0 3-[(S)-2-Benzyloxycarbonylamino-4-(trityl-carbamoyl)-butyrylamino]-thiophene-2-carboxylic acid 
• 17721-06-1 3-aminothiophene 
• 213390-57-9 3-{[(benzyloxy)carbonyl]amino}thiophene-2-carboxylic acid 
• 194088-67-0 3-[(S)-2-(3-Phenyl-ureido)-propionylamino]-thiophene-2-carboxylic acid 
• 194088-68-1 3-[(S)-2-(3-Benzyl-ureido)-propionylamino]-thiophene-2-carboxylic acid 
• 194088-66-9 3-[(S)-2-(Toluene-4-sulfonylamino)-propionylamino]-thiophene-2-carboxylic acid 
• 194088-57-8 3-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-thiophene-2-carboxylic acid 

Relevant articles and documents

POLY-ADP RIBOSE POLYMERASE (PARP) INHIBITORS

The present invention is related to a pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of poly(ADP-ribose)polymerase (PARP). The definitions of the variables are provided herein.

Thiophene/thiazole-benzene replacement on guanidine derivatives targeting α2-Adrenoceptors

Searching for improved antagonists of α2-adrenoceptors, a thorough theoretical study comparing the aromaticity of phenyl-, pyridinyl-, thiophenyl- and thiazolylguanidinium derivatives has been carried out [at M06-2X/6–311++G(p,d) computational level] confirming that thiophene and thiazole will be good ‘ring equivalents’ to benzene in these guanidinium systems. Based on these results, a small but chemically diverse library of guanidine derivatives (15 thiophenes and 2 thiazoles) were synthesised to explore the effect that the bioisosteric change has on affinity and activity at α2-adrenoceptors in comparison with our previously studied phenyl derivatives. All compounds were tested for their α2-adrenoceptor affinity and unsubstituted guanidinothiophenes displayed the strongest affinities in the same range as the phenyl analogues. In the case of cycloakyl systems, thiophenes with 6-membered rings showed the largest affinities, while for the thiazoles the 5-membered analogue presented the strongest affinity. From all the compounds tested for noradrenergic activity, only one compound exhibited agonistic activity, while two compounds showed very promising antagonism of α2-adrenoceptors.

Synthesis of Thieno[3,2-e][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction

A series of 5-substituted thieno[3,2-e][1,4]diazepin-2-ones was synthesized in four steps from methyl 3-aminothiophene-2-carboxylate. After the coupling of 3-aminothiophene with α-amino acids, the key final step that involves an uncatalysed Pictet-Spengler reaction allowed the cyclization of the seven-membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers. A new synthetic approach that uses an uncatalysed Pictet-Spengler cyclization reaction has been developed to access [3,2-e]-type fused thienodiazepinones.