Methyl diethylphosphonoacetate

Base Information

• Chemical Name: Methyl diethylphosphonoacetate
• CAS No.: 1067-74-9
• Molecular Formula: C7H15O5P
• Molecular Weight: 210.167
• Hs Code.: 29310095
• European Community (EC) Number: 213-938-2
• NSC Number: 147757
• DSSTox Substance ID: DTXSID50147732
• Nikkaji Number: J21.052H
• Wikidata: Q72490087
• Mol file: 1067-74-9.mol

Synonyms:Methyl diethylphosphonoacetate;1067-74-9;methyl 2-(diethoxyphosphoryl)acetate;methyl 2-diethoxyphosphorylacetate;Acetic acid, (diethoxyphosphinyl)-, methyl ester;C7H15O5P;methyldiethylphosphonoacetate;Diethylmethylphosphonoacetate;Methyl P,P-diethylphosphonoacetate;Diethyl carbomethoxymethylphosphonate;methyl 2-(diethyl phosphono)acetate;EINECS 213-938-2;MFCD00009081;NSC 147757;(Methoxycarbonylmethyl) diethoxyphosphine oxide;Methyl (diethoxyphosphoryl)acetate;Diethylphosphonoacetic Acid Methyl Ester;methyl diethyl phosphonoacetate;SCHEMBL337596;methyl (diethylphosphono)acetate;Methyl-(diethylphosphono)acetate;AMY3768;DTXSID50147732;BCP24422;Methyl (diethoxyphosphoryl)acetate #;Methyl diethylphosphonoacetate, 97%;AC7892;NSC147757;(Diethoxyphosphinyl)acetic acid methyl;AKOS015899803;diethyl methoxycarbonylmethylphosphonate;CS-W019238;GS-3124;NSC-147757;diethyl(methoxycarbonylmethyl)phosphonate;SY011275;(diethoxyphosphoryl)acetic acid methyl ester;D2873;FT-0605376;EN300-210183;A801502;Acetic acid, phosphono-, p,p-diethyl c-methyl ester;J-001647;[(Methoxycarbonyl)methyl]phosphonic acid diethyl ester

Chemical Property of Methyl diethylphosphonoacetate

Chemical Property:

• Appearance/Colour: Clear colorless to slightly yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 270.2 °C at 760 mmHg
• Flash Point: 131.2 °C
• PSA: 71.64000
• Density: 1.139 g/cm³
• LogP: 1.42550
• Storage Temp.: Store at
• Solubility.: Miscible with tetrahydrofuran.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 210.06571057
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Methyl diethylphosphonoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)OC)OCC
• Uses: Methyl diethylphosphonoacetate is used as a reagent in the preparation of allylic fluorides compounds and in regioselective Diels-Alder reactions. It also serves as a reactant in the preparation of substituted thiophenes and furans, which finds application in type 2 diabetes treatment. Further, it acts as a precursor in the synthesis of pyridone alkaloids and immunosuppressive cyclopentanediol derivatives. In addition to this, it is utilized in the modification of botulinum neurotoxin serotype A protease inhibitors.

Technology Process of Methyl diethylphosphonoacetate

There total 12 articles about Methyl diethylphosphonoacetate 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: 100.0%

bromoacetic acid methyl ester (96-32-2) + triethyl phosphite (122-52-1) → Methyl diethylphosphonoacetate (1067-74-9)

Guidance literature:

at 50 ℃; for 2h;

DOI:10.1016/j.tet.2009.09.104

Reference yield: 98.0%

methyl chloroacetate (96-34-4) + triethyl phosphite (122-52-1) → Methyl diethylphosphonoacetate (1067-74-9)

Guidance literature:

at 135 ℃; for 10h;

DOI:10.1016/j.bmc.2011.02.013

Reference yield: 98.0%

methanol (67-56-1) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → Methyl diethylphosphonoacetate (1067-74-9)

Guidance literature:

scandium tris(trifluoromethanesulfonate); at 64 ℃; for 0.5h;

DOI:10.1055/s-2007-967936

upstream raw materials:

sodium diethyl phosphite

methyl chloroacetate

methanol

(Diethoxyphosphinyl)keten

Downstream raw materials:

monoethylphosphonoacetic acid

3-Methyl-5-phenyl-pent-2-ensaeuremethylester

(E)-3-(4-Benzyloxy-phenyl)-but-2-enoic acid methyl ester

(E)-3-[4-(3-Phenyl-propoxy)-phenyl]-but-2-enoic acid methyl ester

Refernces

• 1、 Sano, Shigeki,Matsumoto, Tomoya,Toguchi, Munehisa,Nakao, Michiyasu. "Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting Garegg-Samuelsson Reaction Conditions". supporting information. p. 1461 - 1464. Retrieved 2018/04/24.
• 2、 Choudhury, Abhijnan Ray,Mukherjee, Santanu. "A catalytic Michael/Horner-Wadsworth-Emmons cascade reaction for enantioselective synthesis of thiochromenes". supporting information. p. 1989 - 1995. Retrieved 2013/08/23.