Thiophene, 3-(4-phenyl-1,3-butadiynyl)-

Base Information

• Chemical Name: Thiophene, 3-(4-phenyl-1,3-butadiynyl)-
• CAS No.: 105836-25-7
• Molecular Formula: C14H8S
• Molecular Weight: 208.284
• Mol file: 105836-25-7.mol

Synonyms:

Chemical Property of Thiophene, 3-(4-phenyl-1,3-butadiynyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thiophene, 3-(4-phenyl-1,3-butadiynyl)-

There total 8 articles about Thiophene, 3-(4-phenyl-1,3-butadiynyl)- 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: 84.0%

3-(bromoethynyl)thiophene (1374225-73-6) + 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3) → 3-(phenylbuta-1,3-diyn-1-yl)thiophene (105836-25-7)

Guidance literature:

With copper(II) ferrite; caesium carbonate; at 100 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jo5011069

Reference yield: 81.0%

3-ethynylthiophene (67237-53-0) + 1-Bromo-2-phenylacetylene (932-87-6) → 3-(phenylbuta-1,3-diyn-1-yl)thiophene (105836-25-7)

Guidance literature:

With bis(acetylacetonate)nickel(II); copper(l) iodide; caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 9h; Inert atmosphere;

DOI:10.1039/c4cc07413k

Reference yield: 66.0%

3-ethynylthiophene (67237-53-0) + 1-Phenylethynyl-1H-1λ3-benzo[d][1,2]iodoxol-3-one → 3-(phenylbuta-1,3-diyn-1-yl)thiophene (105836-25-7)

Guidance literature:

3-ethynylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

1-Phenylethynyl-1H-1λ³-benzo[d][1,2]iodoxol-3-one; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c8ob02375a

upstream raw materials:

3-thiophene carboxaldehyde

((E)-2,3-Dibromo-3-phenyl-allyl)-triphenyl-phosphonium; bromide

trans-(2,3-dibromo-3-phenyl-2-propen-1-yl)triphenylphosphonium bromide

3-(bromoethynyl)thiophene

Refernces

• 1、 Liu, Yashuai,Liu, Ping,Gu, Ningning,Xie, Jianwei,Liu, Yan,Dai, Bin. "Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature". . p. 895 - 900. Retrieved 2016.
• 2、 Mukherjee, Nirmalya,Kundu, Debasish,Ranu, Brindaban C.. "A co-operative Ni-Cu system for Csp-Csp and Csp-Csp2 cross-coupling providing a direct access to unsymmetrical 1,3-diynes and en-ynes". supporting information. p. 15784 - 15787. Retrieved 2015/01/08.