2,5-Diiodo-3-methylthiophene

Base Information

• Chemical Name: 2,5-Diiodo-3-methylthiophene
• CAS No.: 16488-60-1
• Molecular Formula: C5H4 I2 S
• Molecular Weight: 349.96
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10480298
• Nikkaji Number: J389.645E
• Wikidata: Q82314988
• Mol file: 16488-60-1.mol

Synonyms:2,5-DIIODO-3-METHYLTHIOPHENE;16488-60-1;Thiophene, 2,5-diiodo-3-methyl-;Thiophene,2,5-diiodo-3-methyl-;SCHEMBL4613645;DTXSID10480298;AKOS015911766;EN300-203676

Chemical Property of 2,5-Diiodo-3-methylthiophene

Chemical Property:

• PSA: 28.24000
• LogP: 3.26570
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 349.81232
• Heavy Atom Count: 8
• Complexity: 86.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC(=C1)I)I

Technology Process of 2,5-Diiodo-3-methylthiophene

There total 5 articles about 2,5-Diiodo-3-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: 92.0%

3-Methylthiophene (616-44-4,84928-92-7) → 3-methyl-2,5-diiodothiophene (16488-60-1)

Guidance literature:

With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride; In acetic acid; for 4h; Ambient temperature;

DOI:10.1246/bcsj.64.2566

Reference yield: 90.0%

3-Methylthiophene (616-44-4,84928-92-7) → 2-iodo-3-methylthiophene (16494-40-9) + 3-methyl-2,5-diiodothiophene (16488-60-1)

Guidance literature:

With ammonium iodide; dihydrogen peroxide; In water; acetic acid; for 20h; regioselective reaction; Green chemistry;

DOI:10.1139/cjc-2013-0058

Reference yield: 45.0%

3-methyl-2-thiophenecarboxylic acid (23806-24-8) → 3-methyl-2,5-diiodothiophene (16488-60-1)

Guidance literature:

With N-iodo-succinimide; palladium diacetate; In N,N-dimethyl-formamide; at 120 ℃; for 36h; Inert atmosphere; Sealed tube;

upstream raw materials:

3-Methylthiophene

3-methyl-2-thiophenecarboxylic acid

Downstream raw materials:

2,5-dimethoxy-3-methylthiophen

Refernces

• 1、 D'Aleo, Danielle N.,Allard, Sheena R.,Foglia, Cassandra C.,Parent, Shawna L.M.,Rohr, David J.,Gottardo, Christine,MacKinnon, Craig D.. "Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent". . p. 679 - 683. Retrieved 2013/08/23.
• 2、 Hallberg, Anders,Frejd, Torbjoern,Gronowitz, Salo. "Ring-opening Reactions. Part 16. Ring-opening of 2,5-Dimethoxy-3-thienyl-lithium and Some Related Compounds". . p. 1390 - 1392. Retrieved 2007/10/02.