16494-47-6

Basic information

• Product Name: 2,3,4-triiodo-5-methylthiophene
• Synonyms: Thiophene, 2,3,4-triiodo-5-methyl-
• CAS NO: 16494-47-6
• Molecular Formula: C5 H3 I3 S
• Molecular Weight: 475.86
• Product Categories: Thiophens
• Mol File: 16494-47-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 98-100 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 365.1±42.0 °C(Predicted)
• Appearance: /
• Density: 2.948±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4-triiodo-5-methylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-triiodo-5-methylthiophene(16494-47-6)
• EPA Substance Registry System: 2,3,4-triiodo-5-methylthiophene(16494-47-6)

Safety Data

• Hazardous Substances Data: 16494-47-6(Hazardous Substances Data)

Usage

Substituted thiophene molecule

The compound is a variation of the thiophene molecule, which is a five-membered ring with one sulfur atom.

Contains three iodine atoms

The compound has three iodine atoms attached to the thiophene ring, which significantly affect its properties.

Methyl group attached

A methyl group (CH3) is also attached to the thiophene ring, further modifying its properties.

Used in organic synthesis

The compound is utilized as a building block in the creation of more complex organic molecules.

Intermediate in pharmaceutical and agrochemical production

The compound serves as an intermediate in the production of various pharmaceuticals and agrochemicals.

Potential applications in materials science

Due to its unique structure and properties, 2,3,4-triiodo-5-methylthiophene has potential applications in the development of electronic and optical devices.

Upstream product

• 554-14-3 2-Methylthiophene 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 64-17-5 ethanol 
• 1600-27-7 mercury(II) diacetate 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 

Downstream Products

• 16494-35-2 4-iodo-2-methyl-thiophene 
• 16494-37-4 3,4-diiodo-2-methyl-thiophene 
• 19156-50-4 5-methyl-thiophene-3-carboxylic acid 

Relevant articles and documents

The Structure and Characterization of 3,4,5-Triiodo-2-Methylthiophene: An Unexpected Iodination Product of 2-Methylthiophene

Abstract: We report the structure and characterization of 3,4,5-triiodo-2-methylthiophene, obtained as an unexpected, unreported, and significant side product from the iodination of 2-methylthiophene using iodine and iodic acid. Identity of this unexpected product was confirmed by X-ray crystallography and 1H and 13C NMR. The compound crystallizes in the P21/c space group with unit cell parameters a = 16.4183(10) ?, b = 4.1971(3) ?, c = 14.3888(9) ?, β = 111.4442(14), Z = 4, and Dcalc = 3.425?g?cm?3. Analysis of residual electron density maps indicated the presence of crystallographic disorder between the 2-methyl and 5-iodo positions leading to a model of two distinct molecules of 3,4,5-triiodo-2-methylthiophene where the atoms of these two groups were exchanged. Non-covalent iodine–iodine and sulfur–iodine interactions are observed. Graphical Abstract: Three products, two of which are constitutional isomers, are possible when installing multiple iodine atoms on 2-methylthiophene; X-ray structural analysis and spectral characterization show that the 4,5-diiodo isomer is not formed and that the 3,4,5-triiodo isomer is unexpectedly obtained. Halogen and chalcogen bonding are clearly observed. [Figure not available: see fulltext.].