Diazomethyl-phosphonic-acid-diethylester

Base Information

• Chemical Name: Diazomethyl-phosphonic-acid-diethylester
• CAS No.: 25411-73-8
• Molecular Formula: C5H11N2O3P
• Molecular Weight: 178.128
• DSSTox Substance ID: DTXSID90449181
• Nikkaji Number: J781.773H
• Mol file: 25411-73-8.mol

Synonyms:25411-73-8;diazomethyl-phosphonic-acid-diethylester;diethyl diazomethylphosphonate;1-[diazomethyl(ethoxy)phosphoryl]oxyethane;Phosphonic acid, (diazomethyl)-, diethyl ester;DTXSID90449181;NIOUPZZEDGIWIT-UHFFFAOYSA-N;MFCD16876630;Diazomethylphosphonic acid diethyl ester

Chemical Property of Diazomethyl-phosphonic-acid-diethylester

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 178.05072921
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C=[N+]=[N-])OCC

Technology Process of Diazomethyl-phosphonic-acid-diethylester

There total 3 articles about Diazomethyl-phosphonic-acid-diethylester 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:

dimethyl (2-oxopropyl)phosphonate (4202-14-6) → dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With fluorosulfonyl azide; potassium carbonate; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 0.5h; Reagent/catalyst;

Reference yield:

4-acetamidobenzenesulfonyl azide (2158-14-7) → p-acetylaminobenzenesulfonamide (121-61-9) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With triethylamine; dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jo951944n

Reference yield:

dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate (153650-87-4) → p-acetylaminobenzenesulfonamide (121-61-9) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jo951944n

upstream raw materials:

4-acetamidobenzenesulfonyl azide

dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate

dimethyl (2-oxopropyl)phosphonate

Downstream raw materials:

[Diazo-(1-hydroxy-2-oxo-3,3-diphenyl-indan-1-yl)-methyl]-phosphonic acid dimethyl ester

4-(phenylethynyl)anisole

1,2-bis(4-methylphenyl)acetylene

diethyl (1-diazo-2-oxo-2-phenylethyl)phosphonate

Refernces

• 1、 Brown, Dean G.,Velthuisen, Emil J.,Commerford, Jessica R.,Brisbois, Ronald G.,Hoye, Thomas R.. "A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth/Gilbert reagent)". . p. 2540 - 2541. Retrieved 2007/10/03.