2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE

Base Information

• Chemical Name: 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE
• CAS No.: 311321-58-1
• Molecular Formula: C12H7BrS
• Molecular Weight: 263.158
• Mol file: 311321-58-1.mol

Synonyms:2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE

Chemical Property of 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE

Chemical Property:

• PSA: 28.24000
• LogP: 3.91040

Purity/Quality:

2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE

There total 5 articles about 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE 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: 86.0%

1.4-dibromobenzene (106-37-6) + thiophene-2-ylethynylzinc bromide → 2-[2-(4-bromophenyl)ethynyl]thiophene (311321-58-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2017.07.020

Reference yield: 65.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) + 1-[2-(4-bromophenyl)ethynyl]-1H-1,2,3-benzotriazole (476436-59-6) → 2-[2-(4-bromophenyl)ethynyl]thiophene (311321-58-1)

Guidance literature:

thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

1-[2-(4-bromophenyl)ethynyl]-1H-1,2,3-benzotriazole; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; Further stages.;

DOI:10.1021/jo0201575

Reference yield:

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(3-bromophenyl)ethan-1-one (163729-26-8) → 2-[2-(4-bromophenyl)ethynyl]thiophene (311321-58-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: 2N NaOH / tetrahydrofuran / 1 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

3.2: 65 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo0201575

upstream raw materials:

thiophene

1-[2-(4-bromophenyl)ethynyl]-1H-1,2,3-benzotriazole

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(3-bromophenyl)ethan-1-one

1.4-dibromobenzene

Refernces

• 1、 Katritzky, Alan R.,Abdel-Fattah, Ashraf A. A.,Wang, Mingyi. "A novel access to disubstituted acetylenes". . p. 7526 - 7529. Retrieved 2007/10/03.