2-Bromo-5-iodo-3-hexylthiophene

Base Information

• Chemical Name: 2-Bromo-5-iodo-3-hexylthiophene
• CAS No.: 160096-76-4
• Molecular Formula: C10H14BrIS
• Molecular Weight: 373.096
• Hs Code.: 2934999090
• Mol file: 160096-76-4.mol

Synonyms:2-Bromo-3-hexyl-5-iodo-thiophene;

Chemical Property of 2-Bromo-5-iodo-3-hexylthiophene

Chemical Property:

• Refractive Index: 1.5880-1.5920
• Boiling Point: 121°C/0.6mmHg(lit.)
• PSA: 28.24000
• Density: 1.727
• LogP: 5.23800
• Storage Temp.: <0°C

Purity/Quality:

99.5% ^*data from raw suppliers

2-Bromo-3-hexyl-5-iodothiophene (stabilized with Copper chip) >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Bromo-3-hexyl-5-iodothiophene is used as a reactant in the synthesis of structurally defined cationic polythiophenes for DNA binding and gene delivery.

Technology Process of 2-Bromo-5-iodo-3-hexylthiophene

There total 5 articles about 2-Bromo-5-iodo-3-hexylthiophene 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: 97.0%

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ma035396o

Reference yield:

3-hexylthiophene (1693-86-3) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / tetrabutylammonium bromide; methanol; Br₂ / CH₂Cl₂ / 20 °C

2.1: ZnBr₂; tetrabutylammonium tetrafluoroborate / NiBr₂ 2,2'-bipyridine / dimethylformamide / -10.16 °C / Electrolysis

2.2: I₂ / dimethylformamide

With methanol; tetrabutylammomium bromide; tetrabutylammonium tetrafluoroborate; bromine; zinc dibromide; (2,2'-bipyridine)nickel(II) dibromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b006748m

Reference yield:

2,5-dibromo-3-hexylthiophene (116971-11-0) → 2-bromo-5-iodo-3-hexylthiophene (160096-76-4)

Guidance literature:

2,5-dibromo-3-hexylthiophene; With tetrabutylammonium tetrafluoroborate; zinc dibromide; (2,2'-bipyridine)nickel(II) dibromide; In N,N-dimethyl-formamide; at -10.16 ℃; Electrolysis;

With iodine; In N,N-dimethyl-formamide; Further stages.;

DOI:10.1039/b006748m

upstream raw materials:

3-hexyl-2-bromothiophene

2,5-dibromo-3-hexylthiophene

3-hexylthiophene

n-hexylmagnesium bromide

Downstream raw materials:

3-hexyl-2-bromothiophene

C₁₆H₁₉BrS

C₂₆H₃₃BrS₂

C₃₆H₄₇BrS₃

Refernces

• 1、 Lork, Enno,Ramirez Y Medina, Isabel-Maria,Rohdenburg, Markus,Staubitz, Anne. "Aggregation induced emission-emissive stannoles in the solid state". supporting information. p. 9775 - 9778. Retrieved 2020/09/07.
• 2、 He, Lu-Ying,Urrego-Riveros, Sara,Gates, Paul J.,N?ther, Christian,Brinkmann, Maren,Abetz, Volker,Staubitz, Anne. "Synthesis of poly(thiophene-alt-pyrrole) from a difunctionalized thienylpyrrole by Kumada polycondensation". . p. 5399 - 5406. Retrieved 2015/07/15.