Ethyl (diphenylphosphino)acetate

Base Information

• Chemical Name: Ethyl (diphenylphosphino)acetate
• CAS No.: 55552-24-4
• Molecular Formula: C16H17O2P
• Molecular Weight: 272.284
• Hs Code.: 2931900090
• European Community (EC) Number: 259-703-8
• DSSTox Substance ID: DTXSID00204107
• Nikkaji Number: J267.026G
• Wikidata: Q83077555
• Mol file: 55552-24-4.mol

Synonyms:55552-24-4;Ethyl (diphenylphosphino)acetate;ethyl 2-diphenylphosphanylacetate;(ETHOXYCARBONYLMETHYL)DIPHENYLPHOSPHINE;Ethyl 2-(diphenylphosphino)acetate;EINECS 259-703-8;ethyl-2-diphenylphosphinoacetate;SCHEMBL9678408;C16H17O2P;DTXSID00204107;C16-H17-O2-P;MFCD00426223;AKOS017343339;Diphenylphosphinoacetic acid ethyl ester

Chemical Property of Ethyl (diphenylphosphino)acetate

Chemical Property:

• Vapor Pressure: 1.34E-05mmHg at 25°C
• Boiling Point: 367.7 °C at 760 mmHg
• Flash Point: 176.2 °C
• PSA: 39.89000
• LogP: 2.68240
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 272.09661678
• Heavy Atom Count: 19
• Complexity: 250

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CP(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of Ethyl (diphenylphosphino)acetate

There total 16 articles about Ethyl (diphenylphosphino)acetate 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%

ethyl bromoacetate (105-36-2) + diphenylphosphane (829-85-6) → ethyl (diphenylphosphino)acetate (55552-24-4)

Guidance literature:

With cesium hydroxide; 4 Angstroem MS; In N,N-dimethyl-formamide; at 23 ℃; for 20h;

DOI:10.1016/j.tetlet.2003.09.117

Reference yield: 55.0%

chloroacetic acid ethyl ester (105-39-5) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → Tetraphenyldiphosphin (1101-41-3) + ethyl (diphenylphosphino)acetate (55552-24-4)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide; In various solvent(s); Yields of byproduct given; Ambient temperature; elektrochemical reaction, anode Mg bar, cathode stainless steel; var. solv.;

DOI:10.1016/S0040-4039(00)96000-3

Reference yield:

α-Oxo-phenylmethan-diphenylphosphin (36838-04-7) + ethyl bromoacetate (105-36-2) → ethyl (diphenylphosphino)acetate (55552-24-4)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; In toluene; at 80 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152125

upstream raw materials:

ethyl acetate

chloro-diphenylphosphine

chloroacetic acid ethyl ester

diphenylphosphane

Downstream raw materials:

2-benzyl-1-phenyl-2-propene

(2-benzyl-2-hydroxy-3-phenyl)propyldiphenylphosphine oxide

(2-Allyl-2-hydroxy-4-pentenyl)methyl(diphenyl)phosphonium

(2-Hydroxy-2-benzyl-3-phenylpropyl)methyl(diphenyl)phosphonium

Refernces

• 1、 Zhang, Mengyue,Ma, Zhichao,Du, Hongguang,Wang, Zhiqian. "Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source". supporting information. . Retrieved 2020/06/29.
• 2、 Burck, Sebastian,Foerster, Daniela,Gudat, Dietrich. "Phosphorus-carbon bond formation catalysed by electrophilic N-heterocyclic phosphines". . p. 2810 - 2812. Retrieved 2008/09/19.