5751-82-6

Basic information

• Product Name: ETHYL 5-CHLOROTHIOPHENE-2-CARBOXYLATE
• Synonyms: RARECHEM AL BI 0303;Ethyl 5-chloro-2-thiophenecarboxylate;5-Chlorothiophene-2-carboxylic acid ethyl ester;Ethyl 5-chlorothiophene-2-carboxlate;Ethyl 5-chlorothiophene-2-carboxylate, 98+%;2-Thiophenecarboxylic acid, 5-chloro-, ethyl ester;2- chlorinethiophene -5-ethyl forMate;Rivaroxaban impurity P2-O
• CAS NO: 5751-82-6
• Molecular Formula: C₇H₇ClO₂S
• Molecular Weight: 190.65
• Mol File: 5751-82-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 70-71°C 1mm
• Flash Point: 70-71°C/1mm
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.5380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• BRN: 128707
• CAS DataBase Reference: ETHYL 5-CHLOROTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-CHLOROTHIOPHENE-2-CARBOXYLATE(5751-82-6)
• EPA Substance Registry System: ETHYL 5-CHLOROTHIOPHENE-2-CARBOXYLATE(5751-82-6)

Safety Data

• Statements: 36/38
• Safety Statements: 26-36-37
• Hazardous Substances Data: 5751-82-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

InChI:InChI=1/C7H7ClO2S/c1-2-10-7(9)5-3-4-6(8)11-5/h3-4H,2H2,1H3

Upstream product

• 3437-95-4 2-Iodothiophene 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 
• 6310-09-4 2-acetyl-5-chlorothiophene 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 75-03-6 ethyl iodide 
• 2873-18-9 5-bromo-2-chlorothiophene 
• 1609-47-8 diethyl dicarbonate 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 

Downstream Products

• 943780-16-3 (S)-5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-N-(2-phenylpropyl)thiophene-2-carboxamide 
• 943780-19-6 ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylate 
• 943780-18-5 ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate 
• 943780-21-0 5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylic acid 
• 943780-17-4 ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate 
• 1007578-47-3 ethyl 5-(3-{[2,2-bis(ethyloxy)ethyl]oxy}phenyl)-2-thiophene carboxylate 
• 1007578-70-2 5-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide 
• 1007578-72-4 5-(3-Hydroxyphenyl)-2-thiophenecarboxamide 
• 1007578-71-3 ethyl 5-{3-[(2-oxoethyl)oxy]phenyl}-2-thiophenecarboxylate 
• 89640-03-9 ethyl 5‐chloro‐4‐nitrothiophene‐2‐carboxylate 
• 130562-97-9 4,5-dichloro-2-thiophenecarboxylic acid ethyl ester 
• 74168-69-7 5-chloro-2-thiophenemethanol 
• 202336-16-1 5-chlorothiophene-2-carboxamidine hydrochloride 
• 351983-31-8 5-chloro-2-thiophenecarboxylic acid hydrazide 

Relevant articles and documents

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Addressing the Glycine-Rich Loop of Protein Kinases by a Multi-Facetted Interaction Network: Inhibition of PKA and a PKB Mimic

Protein kinases continue to be hot targets in drug discovery research, as they are involved in many essential cellular processes and their deregulation can lead to a variety of diseases. A series of 32 enantiomerically pure inhibitors was synthesized and tested towards protein kinase A (PKA) and protein kinase B mimic PKAB3 (PKA triple mutant). The ligands bind to the hinge region, ribose pocket, and glycine-rich loop at the ATP site. Biological assays showed high potency against PKA, with Ki values in the low nanomolar range. The investigation demonstrates the significance of targeting the often neglected glycine-rich loop for gaining high binding potency. X-ray co-crystal structures revealed a multi-facetted network of ligand-loop interactions for the tightest binders, involving orthogonal dipolar contacts, sulfur and other dispersive contacts, amide-π stacking, and H-bonding to organofluorine, besides efficient water replacement. The network was analyzed in a computational approach.

Synthesis of 2-thiophenecarboxylic and 2,5-thiophenedicarboxylic acid esters via the reaction of thiophenes with the CCl4-ROH reagent in the presence of vanadium, iron, and molybdenum catalysts

2-Thiophenecarboxylic and 2,5-thiohenedicarboxylic acid esters were synthesized via the reaction of thiophene with the CCl4-ROH-catalyst system, with a total yield of 44-85%. A possible reaction scheme includes the successive steps of alkylation of thiophene with carbon tetrachloride, leading to 2-trichloromethylthiophene, and alcoholysis of the product giving the corresponding 2-thiophenecarboxylate. The best catalysts for this reaction are VO(acac)2, Fe(acac)3, and Mo(CO)6.