Tetraethyl dimethylaminomethylenediphosphonate

Base Information

• Chemical Name: Tetraethyl dimethylaminomethylenediphosphonate
• CAS No.: 18855-52-2
• Molecular Formula: C11H27 N O6 P2
• Molecular Weight: 331.286
• Hs Code.: 2922499990
• European Community (EC) Number: 242-627-4
• DSSTox Substance ID: DTXSID30172224
• Nikkaji Number: J224.791G
• Wikidata: Q83042343
• Mol file: 18855-52-2.mol

Synonyms:18855-52-2;Tetraethyl dimethylaminomethylenediphosphonate;1,1-bis(diethoxyphosphoryl)-N,N-dimethylmethanamine;Phosphonic acid, [(dimethylamino)methylene]bis-, tetraethyl ester;Tetraethyl ((dimethylamino)methylene)bisphosphonate;EINECS 242-627-4;Phosphonic acid, P,P'-[(dimethylamino)methylene]bis-, P,P,P',P'-tetraethyl ester;Tetraethyl [(dimethylamino)methylene]bisphosphonate;tetraethyl dimethylaminomethylene diphosphonate;Tetraethyl (dimethylaminomethylene)diphosphonate;SCHEMBL2786870;DTXSID30172224;MFCD00015128;AKOS003599976;CS-0449059;FT-0720781;tetraethyl (dimethylamino)methylenediphosphonate;Tetraethyl ((dimethylamino)methylene)bis(phosphonate);[(Dimethylamino)methylene]bis(phosphonic acid diethyl) ester;[(diethoxy-phosphoryl)-dimethylamino-methyl]-phosphonic acid diethyl ester

Chemical Property of Tetraethyl dimethylaminomethylenediphosphonate

Chemical Property:

• Vapor Pressure: 3.23E-06mmHg at 25°C
• Refractive Index: 1.4590
• Boiling Point: 387.7°Cat760mmHg
• PKA: 4.68±0.50(Predicted)
• Flash Point: 188.3°C
• PSA: 93.92000
• Density: 1.136g/cm³
• LogP: 3.36380
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 331.13136158
• Heavy Atom Count: 20
• Complexity: 313

Purity/Quality:

98%min ^*data from raw suppliers

TETRAETHYL DIMETHYLAMINOMETHYLENEDIPHOSPHONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(N(C)C)P(=O)(OCC)OCC)OCC
• Uses: Tetraethyl (dimethylaminomethylene)diphosphonate undergoes Horner-Wadsworth-Emmons olefination with an aldehyde gives the ?-phosphonato enamine, readily convertible to the homologous acid.

Technology Process of Tetraethyl dimethylaminomethylenediphosphonate

There total 17 articles about Tetraethyl dimethylaminomethylenediphosphonate 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: 93.0%

N-formyldiethylamine (617-84-5) + trifluoromethylsulfonic anhydride (358-23-6) + phosphonic acid diethyl ester (762-04-9) → tetraethyl dimethylaminomethylenediphosphonate (18855-52-2)

Guidance literature:

N-formyldiethylamine; trifluoromethylsulfonic anhydride; With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -78 - 0 ℃;

phosphonic acid diethyl ester; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1021/acs.orglett.5b00004

Reference yield: 75.5%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + triethyl phosphite (122-52-1) → tetraethyl dimethylaminomethylenediphosphonate (18855-52-2)

Guidance literature:

N,N-dimethyl-formamide; With oxalyl dichloride; In diethyl ether; at 20 ℃; for 1h; Cooling;

triethyl phosphite; In diethyl ether; for 1h;

DOI:10.1016/j.bmc.2011.02.022

Reference yield: 72.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + diethyl trimethylsilyl phosphite (13716-45-5) → tetraethyl dimethylaminomethylenediphosphonate (18855-52-2)

Guidance literature:

zinc(II) chloride; at 130 ℃;

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

phosphonic acid diethyl ester

(dimethylaminomethylene)diphosphonic acid

orthoformic acid triethyl ester

Downstream raw materials:

((1E,3E)-1-Dimethylamino-4-phenyl-buta-1,3-dienyl)-phosphonic acid diethyl ester

diethyl phenylacetylphosphonate

[(E)-1-Hydroxy-2-(4-nitro-phenyl)-vinyl]-phosphonic acid diethyl ester

((E)-1-Hydroxy-2-phenyl-vinyl)-phosphonic acid diethyl ester

Refernces

• 1、 Wang, Ai-E.,Chang, Zong,Sun, Wei-Ting,Huang, Pei-Qiang. "General and chemoselective bisphosphonylation of secondary and tertiary amides". supporting information. p. 732 - 735. Retrieved 2015/03/04.
• 2、 O'Boyle, Niamh M.,Greene, Lisa M.,Bergin, Orla,Fichet, Jean-Baptiste,McCabe, Thomas,Lloyd, David G.,Zisterer, Daniela M.,Meegan, Mary J.. "Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones". experimental part. p. 2306 - 2325. Retrieved 2011/05/12.