2-Bromo-3-hexyl-5-formylthiophene

Base Information

• Chemical Name: 2-Bromo-3-hexyl-5-formylthiophene
• CAS No.: 291535-21-2
• Molecular Formula: C₁₁H₁₅BrOS
• Molecular Weight: 275.209
• Mol file: 291535-21-2.mol

Synonyms:4-hexyl-5-bromo-2-thiophenecarboxaldehyde

Chemical Property of 2-Bromo-3-hexyl-5-formylthiophene

Chemical Property:

• Boiling Point: 338.8±42.0 °C(Predicted)
• Density: 1.338±0.06 g/cm3(Predicted)

Purity/Quality:

98% purity ^*data from raw suppliers

5-Bromo-4-hexylthiophene-2-carbaldehyde 98.17% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromo-3-hexyl-5-formylthiophene

There total 2 articles about 2-Bromo-3-hexyl-5-formylthiophene 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: 90.0%

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

Guidance literature:

With trichlorophosphate; In 1,2-dichloro-ethane; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.dyepig.2021.109483

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

Reference yield: 86.3%

4-hexyl-5-bromo-2-thiophenecarboxaldehyde (291535-21-2) + bis(pinacol)diborane (73183-34-3) → 4-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde (1402132-40-4)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tet.2012.08.027

upstream raw materials:

N,N-dimethyl-formamide

2,5-dibromo-3-hexylthiophene

3-hexyl-2-bromothiophene

Downstream raw materials:

HCC(C₄HS)((CH₂)5CH₃)CN

4-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

5'-(4-(diphenylamino)phenyl)-3,4'-dihexyl-[2,2'-bithiophene]-5-carbaldehyde

Refernces

• 1、 Sylvianti, Nadhila,Kim, Youn Hwan,Marsya, Mutia Anissa,Kim, Dong Geun,Ahn, Byung-Hyun,Hong, Seong-Soo,Kim, Joo Hyun. "New A-D-A type small molecules based on benzodithiophene derivative for organic solar cells". . p. 66 - 71. Retrieved 2018.
• 2、 Wu, Jianchang,Ma, Yuchao,Wu, Na,Lin, Yi,Lin, Jian,Wang, Lilei,Ma, Chang-Qi. "2,2-Dicyanovinyl-end-capped oligothiophenes as electron acceptor in solution processed bulk-heterojunction organic solar cells". . p. 28 - 38. Retrieved 2015.
• 3、 Zhang, Qisong,Yu, Peng,Fan, Yong,Sun, Caixia,He, Haisheng,Liu, Xuan,Lu, Lingfei,Zhao, Mengyao,Zhang, Hongxin,Zhang, Fan. "Bright and Stable NIR-II J-Aggregated AIE Dibodipy-Based Fluorescent Probe for Dynamic In Vivo Bioimaging". supporting information. p. 3967 - 3973. Retrieved 2020/12/25.
• 4、 Kim, Dong Geun,Jin, Ho Cheol,Maduwu, Ratna Dewi,Salma, Sabrina Aufar,Moon, Doo Kyung,Kim, Joo Hyun. "Synthesis of new conjugated small-molecule-dyes based on 2-(2-methyl-4H-chromen-4-ylidene)malononitrile as the electron-withdrawing group and their application in photovoltaic devices". . p. 660 - 666. Retrieved 2019/01/04.