Ethynyldiphenylphosphine

Base Information

• Chemical Name: Ethynyldiphenylphosphine
• CAS No.: 6104-47-8
• Molecular Formula: C14H11P
• Molecular Weight: 210.215
• DSSTox Substance ID: DTXSID40447253
• Nikkaji Number: J798.459F
• Wikidata: Q82266099
• Mol file: 6104-47-8.mol

Synonyms:Ethynyldiphenylphosphine;6104-47-8;Phosphine, ethynyldiphenyl-;ETHYNYLDIPHENYLPHOSPHANE;ethynyl(diphenyl)phosphane;diphenylphosphinoacetylene;SCHEMBL3794630;DTXSID40447253;AC8885;MFCD31813881;SY250252;CS-0089413

Chemical Property of Ethynyldiphenylphosphine

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 210.059837349
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CP(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of Ethynyldiphenylphosphine

There total 7 articles about Ethynyldiphenylphosphine 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: 94.0%

chloro-diphenylphosphine (1079-66-9,74391-44-9) + acetylenemagnesium bromide (4301-14-8) → ethynyldiphenylphosphine (6104-47-8)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.0c04212

Reference yield: 92.0%

chloro-diphenylphosphine (1079-66-9,74391-44-9) + trimethylsilylacetylene (1066-54-2) → ethynyldiphenylphosphine (6104-47-8)

Guidance literature:

trimethylsilylacetylene; With ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h;

chloro-diphenylphosphine; In tetrahydrofuran; at -10 - 20 ℃; for 3h;

With potassium carbonate; In methanol; at 20 ℃; for 1.5h;

DOI:10.1515/znb-2020-0047

Reference yield:

ethynylmagnesium chloride (65032-27-1) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → ethynyldiphenylphosphine (6104-47-8)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1246/cl.190647

upstream raw materials:

chloro-diphenylphosphine

acetylenemagnesium bromide

trimethylsilyl(diphenylphosphanyl)acetylene

sodium acetylide

Downstream raw materials:

(1-Hydroxy-cyclohexyl-aethinyl)-diphenyl-phosphin

bis(diphenylphosphino)acetylene

[(η(5)-C5H5)Fe(CO)2(Ph2PC.tplbond.CH)][BF4]

AuC₆F₅(P(C₆H₅)2CCH)

Refernces

• 1、 Hao, Han,Bagnol, Thibault,Pucheault, Mathieu,Schafer, Laurel L.. "Using Catalysts to Make Catalysts: Titanium-Catalyzed Hydroamination to Access P,N-Ligands for Assembling Catalysts in One Pot". supporting information. p. 1974 - 1979. Retrieved 2021/04/05.
• 2、 Okuda, Yasuhiro,Imafuku, Kazuto,Tsuchida, Yoshiyuki,Seo, Tomoyo,Akashi, Haruo,Orita, Akihiro. "Process-Controlled Regiodivergent Copper-Catalyzed Azide-Alkyne Cycloadditions: Tailor-made Syntheses of 4- And 5-Bromotriazoles from Bromo(phosphoryl)ethyne". supporting information. p. 5099 - 5103. Retrieved 2020/07/03.