Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate

Base Information

• Chemical Name: Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate
• CAS No.: 639516-93-1
• Molecular Formula: C16H23O3P
• Molecular Weight: 294.331
• DSSTox Substance ID: DTXSID70514447
• Nikkaji Number: J2.041.273I
• Wikidata: Q82374783
• Mol file: 639516-93-1.mol

Synonyms:639516-93-1;Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate;DTXSID70514447

Chemical Property of Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 294.13848159
• Heavy Atom Count: 20
• Complexity: 370

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC#CC1=CC=CC=C1P(=O)(OCC)OCC

Technology Process of Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate

There total 3 articles about Diethyl [2-(hex-1-yn-1-yl)phenyl]phosphonate 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: 63.0%

hex-1-yne (693-02-7) + 2-(diethoxyphosphonyl)phenyl 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonate (639516-88-4) → (2-hex-1-ynyl-phenyl)-phosphonic acid diethyl ester (639516-93-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 5h;

DOI:10.1021/ja038627f

Reference yield:

(2-hydroxy-phenyl)-phosphonic acid diethyl ester (69646-14-6) → (2-hex-1-ynyl-phenyl)-phosphonic acid diethyl ester (639516-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Et₃N / 8 h / 20 °C

2: 50 percent / PdCl₂(PPh₃)2; Et₃N / dimethylformamide / 4 h / 90 °C

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1002/hc.20156

Reference yield:

C14H14F9O6PS (1335044-31-9) + hex-1-yne (693-02-7) → (2-hex-1-ynyl-phenyl)-phosphonic acid diethyl ester (639516-93-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; Heating; Inert atmosphere;

DOI:10.1016/j.ejmech.2010.01.038

upstream raw materials:

hex-1-yne

2-(diethoxyphosphonyl)phenyl 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonate

(2-hydroxy-phenyl)-phosphonic acid diethyl ester

C₁₄H₁₄F₉O₆PS

Downstream raw materials:

diethyl [2-(2-oxohexyl)phenyl]phosphonate

(2-hex-1-ynylphenyl)phosphonic acid monoethyl ester