N,P-Diphenyl-phosphonamidic acid ethyl ester

Base Information

• Chemical Name: N,P-Diphenyl-phosphonamidic acid ethyl ester
• CAS No.: 78133-05-8
• Molecular Formula: C14H16NO2P
• Molecular Weight: 261.26
• DSSTox Substance ID: DTXSID20999381
• Nikkaji Number: J3.217.708E
• Mol file: 78133-05-8.mol

Synonyms:Benzene ethyl anilidophosphonate;N,P-Diphenyl-phosphonamidic acid ethyl ester;BRN 3531850;Phosphonamidic acid, N,P-diphenyl-, ethyl ester;78133-05-8;C14H16NO2P;SCHEMBL16868425;DTXSID20999381;Ethyl N,P-diphenylphosphonamidate;C14-H16-N-O2-P;Phenylaminophenylethoxyphosphine oxide;LS-106374

Chemical Property of N,P-Diphenyl-phosphonamidic acid ethyl ester

Chemical Property:

• Vapor Pressure: 1.46E-05mmHg at 25°C
• Boiling Point: 366.5°Cat760mmHg
• Flash Point: 175.5°C
• Density: 1.17g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 261.09186575
• Heavy Atom Count: 18
• Complexity: 284

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1=CC=CC=C1)NC2=CC=CC=C2

Technology Process of N,P-Diphenyl-phosphonamidic acid ethyl ester

There total 11 articles about N,P-Diphenyl-phosphonamidic acid ethyl ester 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: 88.0%

Phenylphosphonic acid monoethyl ester amide (5326-06-7) + phenylhydrazine hydrochloride (59-88-1) → ethyl N-phenyl-P-phenylphosphonamidate (78133-05-8)

Guidance literature:

With di-tert-butyl peroxide; copper diacetate; caesium carbonate; In 1,2-dichloro-ethane; at 80 ℃; for 6h;

DOI:10.1080/00397911.2020.1725577

Reference yield: 82.0%

ethyl Phenylphosphinate (172487-18-2,2511-09-3) + Phenyl azide (622-37-7) → ethyl N-phenyl-P-phenylphosphonamidate (78133-05-8)

Guidance literature:

ethyl Phenylphosphinate; Phenyl azide; With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃;

With tetrabutyl ammonium fluoride; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1039/c0cc02472d

Reference yield: 75.0%

ethyl hydrogen phenylphosphonate (4546-19-4) + aniline (62-53-3) → ethyl N-phenyl-P-phenylphosphonamidate (78133-05-8)

Guidance literature:

ethyl hydrogen phenylphosphonate; With N,N-diethyl-1,1,1-trimethylsilanamine; In dichloromethane; at 20 ℃; for 1h;

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h;

aniline; With triethylamine; In acetonitrile; at 50 ℃; for 1h;

DOI:10.1039/c3cc44995e

upstream raw materials:

P,P-dichlorophenylphosphine oxide

ethanol

tetraphenyl-cyclodiphosphazane-2,4-dioxide

aniline

Downstream raw materials:

C₁₈H₂₀NO₄P

C₁₄H₁₅⁽²⁾HNO₂P

Refernces

• 1、 Chen, Xunwei,Luo, Wenjun,Wang, Yanlin,Li, Zikang,Ma, Xiaorui,Peng, Ai-Yun. "Efficient Synthesis of Phosphonamidates through One-Pot Sequential Reactions of Phosphonites with Iodine and Amines". . p. 14474 - 14480. Retrieved 2020/10/06.
• 2、 Wilkening, Ina,Signore, Giuseppe Del,Hackenberger, Christian P. R.. "Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters". supporting information; experimental part. p. 349 - 351. Retrieved 2011/03/17.