(Triphenylphosphoranylidene)ketene

Base Information

• Chemical Name: (Triphenylphosphoranylidene)ketene
• CAS No.: 15596-07-3
• Molecular Formula: C₂₀H₁₅OP
• Molecular Weight: 302.312
• Mol file: 15596-07-3.mol

Synonyms:Ethenone,(triphenylphosphoranylidene)- (9CI); Ketene, (triphenylphosphoranylidene)-(8CI); (Triphenylphosphoranylidene)ethenone;(Triphenylphosphoranylidene)ketene; Bestmann ylide;Ketenylidene(triphenyl)phosphorane; NSC 620573;Oxovinylidenetriphenylphosphorane; Triphenyl(ketenylidene)phosphorane

Chemical Property of (Triphenylphosphoranylidene)ketene

Chemical Property:

• Vapor Pressure: 1.77E-08mmHg at 25°C
• Melting Point: 171 °C
• Refractive Index: 1.604
• Boiling Point: 455.4°C at 760 mmHg
• Flash Point: 229.2°C
• PSA: 26.88000
• Density: 1.12g/cm³
• LogP: 2.76940

Purity/Quality:

98%,99%, ^*data from raw suppliers

(Triphenylphosphoranylidene)ketene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A nucleophilic two-carbon building block that participates in a variety of reactions including cycloaddition, multi-component, and domino reactions.

Technology Process of (Triphenylphosphoranylidene)ketene

There total 9 articles about (Triphenylphosphoranylidene)ketene 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: 91.0%

2-(Trimethylsilyl)-2-(triphenylphosphoranyliden)essigsaeure-trimethylsilylester (141293-41-6) → Hexamethyldisiloxane (107-46-0) + Bestmann ylide (73818-55-0,15596-07-3)

Guidance literature:

at 120 ℃;

Reference yield: 87.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → Bestmann ylide (73818-55-0,15596-07-3)

Guidance literature:

With sodium hexamethyldisilazane; In benzene; at 60 ℃; for 20h;

DOI:10.1021/jo970387x

Reference yield: 84.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → Bestmann ylide (73818-55-0,15596-07-3)

Guidance literature:

With sodium hexamethyldisilazane; In benzene; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2010.09.051

upstream raw materials:

O₂CC(PPh₃)2

2-(Trimethylsilyl)-2-(triphenylphosphoranyliden)essigsaeure-trimethylsilylester

methyl (triphenylphosphoranylidene)acetate

(methyloxycarbonylmethyl)triphenylphosphonium bromide

Downstream raw materials:

2--4-triphenyl-phosphoranyliden-cyclobutandion-(1,3)

1-(1-Pyrazolyl)-2-(triphenylphosphoranyliden)ethanon

2-triphenyl(α-carboxymethylene)phosphorane imidazolide

1-Ethoxy-3H-pyrrolo<1,2-a>indol-3-one

Refernces

• 1、 Aitken, R. Alan,Bjornstad, Vidar,Massil, Tracy,Skramstad, Jan. "Pyrolysis of cyclic polyoxo phosphorus ylides". . p. 577 - 580. Retrieved 1999.
• 2、 Reiter, Dominik,Frisch, Philipp,Szilvási, Tibor,Inoue, Shigeyoshi. "Heavier Carbonyl Olefination: The Sila-Wittig Reaction". . p. 16991 - 16996. Retrieved 2019/10/16.
• 3、 Shie, Jiun-Jie,Liu, Ying-Chih,Hsiao, Jye-Chian,Fang, Jim-Min,Wong, Chi-Huey. "A cell-permeable and triazole-forming fluorescent probe for glycoconjugate imaging in live cells". supporting information. p. 1490 - 1493. Retrieved 2017/02/05.