2-Bromo-3-hexylthiophene

Base Information

• Chemical Name: 2-Bromo-3-hexylthiophene
• CAS No.: 69249-61-2
• Molecular Formula: C10H15BrS
• Molecular Weight: 247.199
• Hs Code.: 29349990
• European Community (EC) Number: 628-938-1
• DSSTox Substance ID: DTXSID20449876
• Nikkaji Number: J524.418H
• Wikidata: Q72456759
• Mol file: 69249-61-2.mol

Synonyms:2-bromo-3-hexylthiophene

Chemical Property of 2-Bromo-3-hexylthiophene

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: n20/D 1.529
• Boiling Point: 272.653 °C at 760 mmHg
• Flash Point: 118.697 °C
• PSA: 28.24000
• Density: 1.275 g/cm³
• LogP: 4.63340
• Storage Temp.: 0-10°C
• Water Solubility.: Slightly miscible with water.
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 246.00778
• Heavy Atom Count: 12
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-hexylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1=C(SC=C1)Br
• Uses: 2-Bromo-3-hexylthiophene is used in the synthesis of End-capped Regioregular Poly(3-hexylthiophene). It is also used to synthesize well-defined head-to-tail-type oligothiophenes which are used in a number of high-technology applications including OLEDs.

Technology Process of 2-Bromo-3-hexylthiophene

There total 11 articles about 2-Bromo-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: 99.0%

3-hexylthiophene (1693-86-3) → 3-hexyl-2-bromothiophene (69249-61-2,125321-66-6)

Guidance literature:

With N-Bromosuccinimide; In acetic acid; at 20 ℃; for 24h;

DOI:10.1039/b703022c

Reference yield: 91.7%

3-hexylthiophene (1693-86-3) → 3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) + 2,5-dibromo-3-hexylthiophene (116971-11-0)

Guidance literature:

With N-Bromosuccinimide; In acetic acid; for 0.833333h; Yields of byproduct given;

DOI:10.1080/00397919908086142

Reference yield: 76.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 2,5-dibromo-3-hexylthiophene (116971-11-0) → 4-hexyl-5-bromo-2-thiophenecarboxaldehyde (291535-21-2) + 3-hexyl-2-bromothiophene (69249-61-2,125321-66-6)

Guidance literature:

2,5-dibromo-3-hexylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Further stages.;

DOI:10.1246/bcsj.80.371

upstream raw materials:

3-hexylthiophene

2,5-dibromo-3-hexylthiophene

N,N-dimethyl-formamide

n-hexylmagnesium bromide

Downstream raw materials:

2-bromo-5-iodo-3-hexylthiophene

3-hexylthiophene

3,3'-dihexyl-2,2'-bithiophene

3,4'-dihexyl-2,2'-bithiophene

Refernces

• 1、 Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang. "Redox-Divergent Construction of (Dihydro)thiophenes with DMSO". supporting information. p. 24284 - 24291. Retrieved 2021/10/08.
• 2、 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.