1,8-bis(phenyl)-3,5-octadiyne

Base Information

• Chemical Name: 1,8-bis(phenyl)-3,5-octadiyne
• CAS No.: 22557-06-8
• Molecular Formula: C₂₀H₁₈
• Molecular Weight: 258.363
• Mol file: 22557-06-8.mol

Synonyms:1,8-bis(phenyl)-3,5-octadiyne

Chemical Property of 1,8-bis(phenyl)-3,5-octadiyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,8-bis(phenyl)-3,5-octadiyne

There total 6 articles about 1,8-bis(phenyl)-3,5-octadiyne 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: 98.0%

4-Phenyl-1-butyne (16520-62-0) → 1,8-bis(phenyl)-3,5-octadiyne (22557-06-8)

Guidance literature:

With copper(l) iodide; ethyl bromoacetate; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo011098i

Reference yield: 38.0%

1,6-dichlorohexa-2,4-diyne (16260-59-6) + benzylmagnesium chloride (6921-34-2) → 1,8-bis(phenyl)-3,5-octadiyne (22557-06-8)

Guidance literature:

benzylmagnesium chloride; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; at -15 ℃; for 0.166667h; Inert atmosphere;

1,6-dichlorohexa-2,4-diyne; In tetrahydrofuran; at -15 - 20 ℃; for 1.36667h; Inert atmosphere;

DOI:10.1039/c7cy00429j

Reference yield: 17.0%

4-Phenyl-1-butyne (16520-62-0) + bromostyrene (103-64-0,1340-14-3) → (E)-hex-1-en-3-yne-1,6-diyldibenzene (1344730-61-5) + 1,8-bis(phenyl)-3,5-octadiyne (22557-06-8)

Guidance literature:

With copper(l) iodide; tetrabutylammonium acetate; potassium carbonate; triphenylphosphine; In water; dimethyl sulfoxide; at 100 ℃; for 24h; Inert atmosphere; Green chemistry;

DOI:10.1016/j.tet.2013.06.063

upstream raw materials:

4-Phenyl-1-butyne

benzyl bromide

bromostyrene

1,6-dichlorohexa-2,4-diyne

Downstream raw materials:

(Z)-1,8-diphenyloct-3-en-5-yne

(E)-2-phenethyl-1,7-diphenylhept-2-en-4-yn-1-ol

Refernces

• 1、 Lei, Aiwen,Srivastava, Manisha,Zhang, Xumu. "Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes". . p. 1969 - 1971. Retrieved 2002.
• 2、 Thiel, Niklas O.,Kemper, Sebastian,Teichert, Johannes F.. "Copper(I)-catalyzed stereoselective hydrogenation of 1,3-diynes and enynes". supporting information. p. 5023 - 5028. Retrieved 2017/07/27.
• 3、 Narani, Anand,Marella, Ravi Kumar,Ramudu, Pochamoni,Rama Rao, Kamaraju Seetha,Burri, David Raju. "Cu(ii) complex heterogenized on SBA-15: A highly efficient and additive-free solid catalyst for the homocoupling of alkynes". . p. 3774 - 3781. Retrieved 2014/01/06.