1-(p-Tosyloxy)-3-phenyl-2-propyne

Base Information

• Chemical Name: 1-(p-Tosyloxy)-3-phenyl-2-propyne
• CAS No.: 21541-60-6
• Molecular Formula: C16H14 O3 S
• Molecular Weight: 286.351
• Hs Code.: 2906299090
• Mol file: 21541-60-6.mol

Synonyms:2-Propyn-1-ol,3-phenyl-, 4-methylbenzenesulfonate (9CI); 2-Propyn-1-ol, 3-phenyl-,p-toluenesulfonate (8CI); 3-Phenylpropargyl 4-toluenesulfonate;3-Phenylpropargyl tosylate; Phenylpropargyl tosylate

Chemical Property of 1-(p-Tosyloxy)-3-phenyl-2-propyne

Chemical Property:

• Melting Point: 76-77 °C(Solv: chloroform (67-66-3))
• Boiling Point: 445.0±28.0 °C(Predicted)
• PSA: 51.75000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 3.83280

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(p-Tosyloxy)-3-phenyl-2-propyne

There total 5 articles about 1-(p-Tosyloxy)-3-phenyl-2-propyne 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%

3-Phenyl-2-propyn-1-ol (1504-58-1) + p-toluenesulfonyl chloride (98-59-9) → 3-phenylprop-2-ynyl 4-methylbenzenesulfonate (21541-60-6)

Guidance literature:

With potassium hydroxide; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1039/c7cc01759f

Reference yield:

phenylacetylene (536-74-3) → 3-phenylprop-2-ynyl 4-methylbenzenesulfonate (21541-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium hydroxide / diethyl ether / 0.5 h / 0 °C

With n-butyllithium; potassium hydroxide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ol201395p

Reference yield:

bromobenzene (108-86-1,52753-63-6) → 3-phenylprop-2-ynyl 4-methylbenzenesulfonate (21541-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C

2: potassium hydroxide / dichloromethane / 1 h / 0 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; potassium hydroxide; In dichloromethane; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1039/c4ra11035h

upstream raw materials:

3-Phenyl-2-propyn-1-ol

p-toluenesulfonyl chloride

phenylacetylene

bromobenzene

Downstream raw materials:

N-(3-phenylprop-2-ynyl)ephedrine

phenyl (3-phenylprop-2-yn-1-yl) sulfide

1-phenyl-3-phenylsulphonylpropadiene

trans-cinnamyl phenyl sulfone

Refernces

• 1、 Tomita, Ren,Koike, Takashi,Akita, Munetaka. "Photoredox-catalyzed oxytrifluoromethylation of allenes: Stereoselective synthesis of 2-trifluoromethylated allyl acetates". supporting information. p. 4681 - 4684. Retrieved 2017/07/10.
• 2、 Zhu, Na,Wang, Fei,Chen, Pinhong,Ye, Jinxing,Liu, Guosheng. "Copper-Catalyzed Intermolecular Trifluoromethylazidation and Trifluoromethylthiocyanation of Allenes: Efficient Access to CF3-Containing Allyl Azides and Thiocyanates". supporting information. p. 3580 - 3583. Retrieved 2015/07/28.