Ethyl dimethylphosphonoacetate

Base Information

• Chemical Name: Ethyl dimethylphosphonoacetate
• CAS No.: 311-46-6
• Molecular Formula: C6H13O5P
• Molecular Weight: 196.14
• Hs Code.: 2931900090
• European Community (EC) Number: 206-222-6
• DSSTox Substance ID: DTXSID00185043
• Nikkaji Number: J193.727H
• Wikidata: Q72474572
• Mol file: 311-46-6.mol

Synonyms:Ethyl dimethylphosphonoacetate;311-46-6;ethyl 2-(dimethoxyphosphoryl)acetate;Ethyl (dimethoxyphosphinoyl)acetate;ethyl 2-dimethoxyphosphorylacetate;Acetic acid, (dimethoxyphosphinyl)-, ethyl ester;EINECS 206-222-6;MFCD00015677;DIMETHYL(ETHOXYCARBONYLMETHYL)PHOSPHONATE;Ethyl (dimethoxyphosphoryl)acetate;ethyl dimethyl phosphonoacetate;ethyl(dimethylphosphono)acetate;SCHEMBL639641;HUNISAHOCCASGM-UHFFFAOYSA-;AMY3931;DTXSID00185043;BCP24421;ethyl[bis(methyloxy)phosphoryl]acetate;AKOS015899895;CS-W022647;ethyl [bis(methyloxy)phosphoryl]acetate;Dimethylphosphonoacetic Acid Ethyl Ester;AS-15164;Dimethoxyphosphinylacetic acid ethyl ester;SY006735;E1160;FT-0631932;A876017;Acetic acid, 2-(dimethoxyphosphinyl)-, ethyl ester;W-106914;Ethyl dimethylphosphonoacetate, technical, >=90% (GC)

Chemical Property of Ethyl dimethylphosphonoacetate

Chemical Property:

• Vapor Pressure: 2.46E-05mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 268.691 °C at 760 mmHg
• Flash Point: 98.889 °C
• PSA: 71.64000
• Density: 1.168 g/cm³
• LogP: 1.03540
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 196.05006051
• Heavy Atom Count: 12
• Complexity: 182

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Dimethylphosphonoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CP(=O)(OC)OC
• Uses: Reactant for synthesis of: Non-nucleoside inhibitors of HCV polymerase NS5BNeuropeptide Y1 receptor antagonistsAlkenylcarboxylates from Horner-Wadsworth-Emmons reactionsReactant for: Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A Intramolecular Michael reactionsOlefination of peptidyl aldehydes with stabilized ylides

Technology Process of Ethyl dimethylphosphonoacetate

There total 8 articles about Ethyl dimethylphosphonoacetate 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: 84.0%

chloroacetic acid ethyl ester (105-39-5) + phosphorous acid trimethyl ester (121-45-9) → ethyl 2-(dimethoxyphosphoryl)acetate (311-46-6)

Guidance literature:

In toluene; at 150 ℃; for 0.166667h; under 3750.38 - 15001.5 Torr; Large scale;

Reference yield: 76.0%

methanol (67-56-1) + ethyl diphenylphosphonoacetate (16139-79-0) → ethyl 2-(dimethoxyphosphoryl)acetate (311-46-6) + ethyl methylphenylphosphonoacetate (625396-71-6,852573-54-7)

Guidance literature:

With 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1248/cpb.53.131

Reference yield: 35.0%

diazoacetic acid ethyl ester (623-73-4) + phosphorous acid trimethyl ester (121-45-9) → ethyl 2-(dimethoxyphosphoryl)acetate (311-46-6)

Guidance literature:

With lithium bromide; (5,10,15,20-tetraphenylporphyrinato)cobalt(II); In toluene; at 80 ℃; for 48h;

DOI:10.1016/j.tet.2008.05.108

upstream raw materials:

methanol

(2-chloro-2-ethoxy-vinyl)-phosphonic acid dichloride

chloroacetic acid ethyl ester

phosphorous acid trimethyl ester

Downstream raw materials:

ethyl cinnamate-3-d

ethyl 2E,4E-decadienoate

ethyl trans-2, cis-6-dodecadienoate

ethyl 3-(2-benzenesulfonyloxy-3-methoxy-6-nitrophenyl)propenoate

Refernces

• 1、 Ertürk, Erkan,Demir, Ayhan S.. "Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex". . p. 7555 - 7560. Retrieved 2008/12/20.
• 2、 Aggarwal, Varinder K.,Fulton, J. Robin,Sheldon, Chris G.,De Vicente, Javier. "Generation of phosphoranes derived from phosphites. A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig Olefinations". . p. 6034 - 6035. Retrieved 2007/10/03.