2-Iodo-5-methylthiophene

Base Information

• Chemical Name: 2-Iodo-5-methylthiophene
• CAS No.: 16494-36-3
• Molecular Formula: C5H5IS
• Molecular Weight: 224.065
• Hs Code.: 29349990
• European Community (EC) Number: 670-341-3
• DSSTox Substance ID: DTXSID60167825
• Nikkaji Number: J147.944J
• Wikidata: Q72484106
• Mol file: 16494-36-3.mol

Synonyms:2-Iodo-5-methylthiophene;16494-36-3;Thiophene, 2-iodo-5-methyl-;MFCD00022492;C5H5IS;2-iodo-5-methyl-thiophene;SCHEMBL80621;BIDD:GT0402;DTXSID60167825;2-Iodo-5-methylthiophene, 97%;AMY31922;AKOS015854007;CS-W014227;DS-15211;SY016776;A3661;FT-0637370;EN300-646056;J-509717

Chemical Property of 2-Iodo-5-methylthiophene

Chemical Property:

• Vapor Pressure: 0.458mmHg at 25°C
• Refractive Index: n20/D 1.626(lit.)
• Boiling Point: 200.5 °C at 760 mmHg
• Flash Point: 75.1 °C
• PSA: 28.24000
• Density: 1.91 g/cm³
• LogP: 2.66110
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 223.91567
• Heavy Atom Count: 7
• Complexity: 65.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Iodo-5-methylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/38

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(S1)I
• Uses: 2-Iodo-5-methylthiophene may be used for the preparation of:methylbis[2-(5-methyl)thienyl]boranedimethyl-terthienyl5,5′-dimethy-2,2′-bithienyl

Technology Process of 2-Iodo-5-methylthiophene

There total 9 articles about 2-Iodo-5-methylthiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

trimethyl(5-methylthiophen-2-yl)stannane (86134-27-2) → 2-iodo-5-methylthiophene (16494-36-3)

Guidance literature:

With iodine; In tetrahydrofuran; at 0 ℃;

Reference yield: 87.0%

2-Methylthiophene (554-14-3) → 2-iodo-5-methylthiophene (16494-36-3)

Guidance literature:

With N-iodo-succinimide; In chloroform; acetic acid; for 70h; Darkness;

DOI:10.1002/anie.201407377

Reference yield:

2,5-bis-trimethylstannanyl-thiophene (86134-26-1) + methyl iodide (74-88-4) → 2-iodo-5-methylthiophene (16494-36-3) + 2,5-diiodothiophene (625-88-7)

Guidance literature:

With iodine; Yield given. Multistep reaction. Yields of byproduct given;

upstream raw materials:

2-Methylthiophene

trimethyl(5-methylthiophen-2-yl)stannane

2,5-bis-trimethylstannanyl-thiophene

methyl iodide

Downstream raw materials:

2-methylthiophene-5-carboxylic acid

5,5'-dimethyl-2,2'-dithiophene

(Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester

(Z)-1-(5-methylthien-2-yl)-2-(4-methylphenyl)ethene

Refernces

• 1、 D'Auria,Mauriello. "Bis-(trifluoroacetoxy)iodobenzene-iodine system: An efficient and selective reagent for iodination of thiophene derivatives". . p. 4883 - 4884. Retrieved 1995.
• 2、 Bouarfa, Salima,Bentabed-Ababsa, Ghenia,Erb, William,Picot, Laurent,Thiéry, Valérie,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence. "Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines". . p. 1271 - 1284. Retrieved 2020/11/09.
• 3、 Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning. "Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization". supporting information. p. 2886 - 2889. Retrieved 2015/06/30.