16494-40-9

Basic information

• Product Name: 2-Iodo-3-methylthiophene
• Synonyms: 2-Iodo-3-methylthiophene;3-Methyl-2-iodothiophene
• CAS NO: 16494-40-9
• Molecular Formula: C5 H5 I S
• Molecular Weight: 224.06
• Product Categories: Thiophens
• Mol File: 16494-40-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Iodo-3-methylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-3-methylthiophene(16494-40-9)
• EPA Substance Registry System: 2-Iodo-3-methylthiophene(16494-40-9)

Safety Data

• Hazardous Substances Data: 16494-40-9(Hazardous Substances Data)

Usage

General Description

2-Iodo-3-methylthiophene is a chemical compound with the molecular formula C5H5IS. It is a substituted thiophene with an iodine atom attached to the second carbon and a methyl group attached to the third carbon of the five-membered ring. 2-Iodo-3-methylthiophene is commonly used as a building block in organic synthesis for the production of pharmaceuticals, agrochemicals, and advanced materials. It is known for its strong electronic properties and has been studied for its potential use in organic electronic devices and optoelectronic applications. Additionally, 2-Iodo-3-methylthiophene is also used as a reagent in chemical reactions to introduce a functional group onto a molecule or to create new carbon-carbon bonds. Despite its potential utility, this compound should be handled with care, as it is classified as a hazardous material and may cause skin and eye irritation, as well as respiratory and other adverse effects if not handled properly.

Upstream product

• 616-44-4 3-Methylthiophene 

Downstream Products

• 99708-90-4 2-(hydroxymethyl)-3-(p-toluenesulfinylmethyl)thiophene 
• 99708-85-7 2-cyano-3-(p-toluenesulfenylmethyl)thiophene 
• 99708-87-9 3-(p-toluenesulfinylmethyl)thiophene-2-carboxaldehyde 
• 59961-15-8 methyl 3-(bromomethyl)thiophene-2-carboxylate 
• 81452-50-8 methyl 3-(tosylmethyl)thiophene-2-carboxylate 
• 81458-99-3 methyl 3-(p-toluenesulfinylmethyl)thiophene-2-carboxylate 
• 99708-83-5 2-cyano-3-(tosylmethyl)thiophene 
• 99708-86-8 3-(tosylmethyl)thiophene-2-carboxaldehyde 
• 99708-89-1 2-(hydroxymethyl)-3-(tosylmethyl)thiophene 
• 99708-82-4 methyl 3-(p-toluenesulfenylmethyl)thiophene-2-carboxylate 
• 99708-84-6 2-cyano-3-(p-toluenesulfinylmethyl)thiophene 
• 81452-54-2 methyl 3-methylthiophene-2-carboxylate 
• 55406-13-8 3-methylthiophene-2-carbonitrile 

Relevant articles and documents

Extended Orthogonally Fused Conducting Oligomers for Molecular Electronic Devices

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A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans. The Royal Society of Chemistry 2010.

Thallium(III) Trifluoroacetate-Trifluoroacetic Acid in the Chemistry of Polythiophenes. 2. Treatment of 3-Alkylthiophenes and Electron Paramagnetic Resonance Results

The treatment of thiophene and 3-alkylthiophenes with thallium(III) trifluoroacetate (TTFA) in trifluoroacetic acid (TFA) gives insoluble and dark powdery solids with oxygen content and electrical conductivities ranging from 10-4 to 10-6 Ω-1 cm-1. Polar and short fractions are negligible. All of them show semiconductivity (10-3Ω-1 cm-1) when doped in iodine atmosphere. Electron paramagnetic resonance (EPR) spectra of either as-synthesized or I2-treated solids display characteristic single and broad lines (ΔHPP, 1.84-7.4 G) with Lorentzian shapes and g-values in the range 2.0028-2.0038. Infrared spectra show characteristic C-H out-of-plane deformations (780 cm-1 for polythiophene and 820-825 cm-1 for poly(3-alkylthiophenes)) in addition to a strong peak at 1650-1690 cm-1 which has not been conclusively assigned. EPR spectra of some disubstituted and tetrasubstituted 2,2′-bithiophene radical cations have been observed and their g-values and coupling constants assigned when the corresponding parent compounds are photolyzed with ultraviolet light in TFA. Photolysis of 3-alkylthiophenes in TFA in the EPR instrument gave the radical cations of 4,4′-dialkyl-2,2′-bithiophenes. In no case, were EPR signals of the isomeric 3,3′-dialkyl- or 3,4′-dialkyl-2,2′-bithiophene radical cations observed, indicating that dimerization of 3-alkylthiophenes occurs through the less sterically hindered 5-position. The presence of two doublet species corresponding to both conformers, syn and anti, in the radical cations is associated with a large barrier to rotation about the C(2)-C(2′) bond.