Diethyl (2,5-dioxoimidazolidin-4-yl)phosphonate

Base Information

• Chemical Name: Diethyl (2,5-dioxoimidazolidin-4-yl)phosphonate
• CAS No.: 95378-36-2
• Molecular Formula: C7H13 N2 O5 P
• Molecular Weight: 236.164
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00393222
• Nikkaji Number: J434.388C
• Mol file: 95378-36-2.mol

Synonyms:95378-36-2;diethyl (2,5-dioxoimidazolidin-4-yl)phosphonate;diethyl 5-hydantoylphosphonate;5-diethoxyphosphorylimidazolidine-2,4-dione;Phosphonic acid, (2,5-dioxo-4-imidazolidinyl)-, diethyl ester;Diethyl (2,5-dioxo-4-imidazolidinyl)phosphonate;5-(Diethoxyphosphinyl)hydantoin;SCHEMBL1934137;DTXSID00393222;methyltitanium(iv) triisopropoxide;PNQYQNIOVAYJJG-UHFFFAOYSA-N;STR08723;MFCD00835392;AKOS024371034;diethyl 2,4-dioxoimidazoline-5-phosphonate;diethyl 2,4-dioxoimidazolidine-5-phosphonate;FT-0624830;F20864

Chemical Property of Diethyl (2,5-dioxoimidazolidin-4-yl)phosphonate

Chemical Property:

• Melting Point: 159-161°C
• Refractive Index: 1.485
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 103.87000
• Density: 1.35g/cm³
• LogP: 0.66520
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 236.05620852
• Heavy Atom Count: 15
• Complexity: 309

Purity/Quality:

98%Min ^*data from raw suppliers

Diethyl 5-hydantoylphosphonate, 96% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1C(=O)NC(=O)N1)OCC

Technology Process of Diethyl (2,5-dioxoimidazolidin-4-yl)phosphonate

There total 4 articles about Diethyl (2,5-dioxoimidazolidin-4-yl)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: 83.0%

5-bromohydantoin (173904-10-4) + triethyl phosphite (122-52-1) → diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate (95378-36-2)

Guidance literature:

In 1,4-dioxane; at 40 - 45 ℃; for 1.5h;

DOI:10.1016/j.jcat.2004.05.021

Reference yield:

2-Amino-2-(diethoxyphosphoryl)essigsaeure-ethylester (79428-78-7) → diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate (95378-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / 2N HCl / ethanol; H₂O / 72 h / Ambient temperature

2: 35 percent / sodium / ethanol / 24 h / Ambient temperature

With hydrogenchloride; sodium; In ethanol; water;

Reference yield:

2,4-imidazolidinedione (461-72-3) + triethyl phosphite (122-52-1) → diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate (95378-36-2)

Guidance literature:

2,4-imidazolidinedione; With bromine; acetic acid;

triethyl phosphite;

DOI:10.1021/op900216v

upstream raw materials:

5-bromohydantoin

triethyl phosphite

2-Amino-2-(diethoxyphosphoryl)essigsaeure-ethylester

2,4-imidazolidinedione

Downstream raw materials:

5-[1-(2,4,6-Trimethoxy-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione

5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(E)-ylidene]-imidazolidine-2,4-dione

5-[1-(2,3,4-Trimethoxy-6-nitro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

5-(2-nitro-benzylidene)-imidazolidine-2,4-dione

Refernces

• 1、 Tinto, Francesco,Pagano, Dario,Manzo, Emiliano. "Synthesis of parazoanthine B and analogs". . p. 4379 - 4384. Retrieved 2015/06/08.
• 2、 Alimardanov, Asaf,Nikitenko, Antonia,Connolly, Terrence J.,Feigelson, Gregg,Chan, Anita W.,Ding, Zhixian,Ghosh, Mousumi,Shi, Xinxu,Ren, Jianxin,Hansen, Eric,Farr, Roger,MacEwan, Michael,Tadayon, Sam,Springer, Dane M.,Kreft, Anthony F.,Ho, Douglas M.,Potoski, John R.. "Practical enantioselective synthesis of a 3-aryl-3-trifluoromethyl-2- aminopropanol derivative". scheme or table. p. 1161 - 1168. Retrieved 2010/04/22.