Trimethyl phosphonoacetate

Base Information

• Chemical Name: Trimethyl phosphonoacetate
• CAS No.: 5927-18-4
• Deprecated CAS: 51298-31-8
• Molecular Formula: C5H11O5P
• Molecular Weight: 182.113
• Hs Code.: 29310095
• European Community (EC) Number: 227-663-0
• NSC Number: 84262
• DSSTox Substance ID: DTXSID3064063
• Nikkaji Number: J227E
• Wikidata: Q72514300
• Metabolomics Workbench ID: 67947
• Mol file: 5927-18-4.mol

Synonyms:trimethylacetyl phosphate

Chemical Property of Trimethyl phosphonoacetate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.000577mmHg at 25°C
• Melting Point: 242 °C
• Refractive Index: n20/D 1.437(lit.)
• Boiling Point: 311 ºC at 760 mmHg
• Flash Point: 109.7 °C
• PSA: 71.64000
• Density: 1.125 g/cm³
• LogP: 0.64530
• Storage Temp.: Store below +30°C.
• Water Solubility.: Slightly miscible with water.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 182.03441044
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

TmpA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CP(=O)(OC)OC
• Uses: Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.

Technology Process of Trimethyl phosphonoacetate

There total 9 articles about Trimethyl phosphonoacetate 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: 88.0%

methanol (67-56-1) + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → trimethyl phosphonoacetate (5927-18-4) + methyl methyl(2,2,2-trifluoroethyl)phosphonoacetate (681123-85-3)

Guidance literature:

With triethylamine; at 20 ℃; for 0.5h;

DOI:10.1248/cpb.53.131

Reference yield: 74.0%

bromoacetic acid methyl ester (96-32-2) + phosphorous acid trimethyl ester (121-45-9) → trimethyl phosphonoacetate (5927-18-4)

Guidance literature:

at 100 ℃; for 12h;

Reference yield: 70.0%

methyl chloroacetate (96-34-4) + phosphorous acid trimethyl ester (121-45-9) → trimethyl phosphonoacetate (5927-18-4)

Guidance literature:

Heating;

upstream raw materials:

methanol

phosphonoacetic acid

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

methyl chloroacetate

Downstream raw materials:

Cyclopentylideneacetic acid methyl ester

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-4-C--α-D-erythro-hexopyranoside

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-4-C--α-D-erythro-hexopyranoside

benzyl 2-deoxy-3,4-O-isopropylidene-2C<(E)-methoxycarbonylmethylene>-β-L-erythro-pentopyranoside

Refernces

• 1、 Sano, Shigeki,Kujime, Eiko,Takemoto, Yuka,Shiro, Motoo,Nagao, Yoshimitsu. "A facile synthesis of novel chiral phosphonoacetates bearing a stereogenic phosphorus atom". . p. 131 - 134. Retrieved 2007/10/03.
• 2、 Mahipal Reddy,Raj Gopal,Jayathirtha Rao. "Electronic effects on the Z(cis)-selectivity of Horner-Wadsworth-Emmons olefination reaction". . p. 312 - 317. Retrieved 2007/10/03.