88105-22-0

Basic information

• Product Name: Methyl 5-iodothiophene-2-carboxylate
• Synonyms: Methyl 5-iodothiophene-2-carboxylate;5-iodo-2-Thiophenecarboxylic acid methyl ester
• CAS NO: 88105-22-0
• Molecular Formula: C₆H₅IO₂S
• Molecular Weight: 268.07217
• Mol File: 88105-22-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: Methyl 5-iodothiophene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-iodothiophene-2-carboxylate(88105-22-0)
• EPA Substance Registry System: Methyl 5-iodothiophene-2-carboxylate(88105-22-0)

Safety Data

• Hazardous Substances Data: 88105-22-0(Hazardous Substances Data)

Usage

Description

Methyl 5-iodothiophene-2-carboxylate is a chemical compound with the molecular formula C7H5IO2S. It is a derivative of thiophene, which is a heterocyclic aromatic compound containing a five-membered ring of four carbon atoms and one sulfur atom. The presence of an iodine atom and a carboxylate group in the compound makes it a versatile building block for the synthesis of various pharmaceuticals, agrochemicals, and advanced materials.

Uses

Used in Pharmaceutical Industry:
Methyl 5-iodothiophene-2-carboxylate is used as a building block for the synthesis of complex molecules with potential biological applications. Its unique structure and reactivity make it a valuable tool for the development of new pharmaceuticals.
Used in Agrochemical Industry:
Methyl 5-iodothiophene-2-carboxylate is used as a precursor for the preparation of agrochemicals, contributing to the development of new and effective products for agricultural applications.
Used in Advanced Materials:
Methyl 5-iodothiophene-2-carboxylate is used in the synthesis of advanced materials, such as organic semiconductors and conductive polymers, due to its versatile chemical properties and potential for creating complex molecular structures.
Used in Organic Synthesis:
Methyl 5-iodothiophene-2-carboxylate is used as a precursor in organic synthesis for the preparation of complex molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structure and reactivity make it a valuable tool for chemical research and product development.

Upstream product

• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 144-55-8 sodium hydrogencarbonate 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 3437-95-4 2-Iodothiophene 
• 67-56-1 methanol 
• 558-13-4 carbon tetrabromide 
• 56-23-5 tetrachloromethane 

Downstream Products

• 125972-73-8 5-Furan-2-ylethynyl-thiophene-2-carbaldehyde 
• 125972-75-0 methyl 5-(phenylethynyl)-thiophene-2-carboxylate 
• 819863-79-1 2-(4-tert-butyl-phenyl)-5-(5-iodo-thiophen-2-yl)-[1,3,4]oxadiazole 
• 819863-82-6 2-(4-tert-butylphenyl)-5-(4-ethynylthienyl)-1,3,4-oxadiazole 
• 1027961-21-2 5-iodo-thiophene-2-carboxylic acid N'-(4-tert-butyl-benzoyl)-hydrazide 
• 819863-80-4 4-{5-[5-(4-tert-butyl-phenyl)-[1,3,4]oxadiazol-2-yl]-thiophen-2-yl}-2-methyl-but-3-yn-2-ol 
• 60166-85-0 5-Iodo-thiophene-2-carboxylic acid 
• 1150847-28-1 methyl 5-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)thiophene-2-carboxylate 

Relevant articles and documents

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

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.

Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent

Benzyltrimethylammonium dichloroiodate, previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group.