1-(p-Tosyloxy)-2-pentyne

Base Information

• Chemical Name: 1-(p-Tosyloxy)-2-pentyne
• CAS No.: 92666-05-2
• Molecular Formula: C12H14 O3 S
• Molecular Weight: 238.307
• Hs Code.: 2905290000
• Mol file: 92666-05-2.mol

Synonyms:2-Pentyn-1-ol,4-methylbenzenesulfonate (9CI); 2-Pentyn-1-yl tosylate; 2-pentynyl tosylate

Chemical Property of 1-(p-Tosyloxy)-2-pentyne

Chemical Property:

• PSA: 51.75000
• LogP: 3.19450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(p-Tosyloxy)-2-pentyne

There total 2 articles about 1-(p-Tosyloxy)-2-pentyne 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%

pent-2-yn-1-ol (6261-22-9) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid pent-2-ynyl ester (92666-05-2)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 0.333333h; Ambient temperature;

Reference yield: 64.0%

pent-2-yn-1-ol (6261-22-9) + p-toluenesulfonyl chloride (98-59-9) → 1-chloropent-2-yne (22592-15-0) + toluene-4-sulfonic acid pent-2-ynyl ester (92666-05-2)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00089

Reference yield: 96.0%

(phenylethynyl)dimethylaluminum (1007-47-2) + toluene-4-sulfonic acid pent-2-ynyl ester (92666-05-2) → (hepta-1,4-diynyl)benzene

Guidance literature:

In n-heptane; dichloromethane; at 0 ℃; for 1h;

DOI:10.1055/s-2007-990885

upstream raw materials:

pent-2-yn-1-ol

p-toluenesulfonyl chloride

Downstream raw materials:

octa-2,5-diyn-1-ol

1-bromo-pent-2-yne

(Z,Z)-1-hydroxynona-3,6-diene

(3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate

Refernces

• 1、 Anderson, Edward A.,Elbert, bryony L.,Llaveria, Josep,Streatfeild, penelope E.,Urbitsch, Felix. "A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids". supporting information. . Retrieved 2020/02/28.
• 2、 Xu, Kai,Zhao, Shuai,Xu, Jia-Kuan,Shan, Ming-Wei,Yu, Jia-Li,Wang, Yu-Bo,Zhang, Cheng-Fang,Chen, Xin. "Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes". supporting information. p. 1848 - 1853. Retrieved 2017/10/10.