Phosphonoacetic acid

Base Information

• Chemical Name: Phosphonoacetic acid
• CAS No.: 4408-78-0
• Molecular Formula: C2H5O5P
• Molecular Weight: 140.032
• Hs Code.: 29319019
• European Community (EC) Number: 224-558-1,253-297-6
• NSC Number: 18205
• UNII: N919E46723
• DSSTox Substance ID: DTXSID2045107
• Nikkaji Number: J138.397C
• Wikidata: Q27093778
• NCI Thesaurus Code: C84056
• Metabolomics Workbench ID: 38469
• ChEMBL ID: CHEMBL50300
• Mol file: 4408-78-0.mol

Synonyms:Disodium Phosphonoacetate;Fosfonet Sodium;Phosphonacetic Acid;Phosphonoacetate;Phosphonoacetate, Disodium;Phosphonoacetic Acid

Chemical Property of Phosphonoacetic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 6E-11mmHg at 25°C
• Melting Point: 143-146 °C(lit.)
• Refractive Index: 1.5180 (estimate)
• Boiling Point: 490.2 °C at 760 mmHg
• PKA: 1.74±0.10(Predicted)
• Flash Point: 250.2 °C
• PSA: 104.64000
• Density: 1.858 g/cm³
• LogP: -0.75130
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: water: soluble100mg/mL, clear to very slightly hazy, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 139.98746025
• Heavy Atom Count: 8
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phosphonoacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(=O)O)P(=O)(O)O
• Uses: Antiviral. Phosphonoacetic acid inhibits deoxyribo nucleic acid polymerase, especially in viruses. It is used as an antiviral agent. Further, it is used in the preparation of 1-(dimethylamino)-2,2-bis[(dimethylimmonio)-methyl]ethene diperchlorate by reacting with phosphorus oxychloride. Phosphonoacetic acid was used as an inhibitor of viral DNA replication, to investigate the infected cell protein 0 (bICP0) localization in infected low passage bovine cells. It was also used as a phosphorus source for microbial growth in phosphate-independent manner.

Technology Process of Phosphonoacetic acid

There total 26 articles about Phosphonoacetic acid 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%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → phosphonoacetic acid (4408-78-0)

Guidance literature:

With hydrogenchloride; for 8h; Heating;

DOI:10.1002/ps.2780400110

Reference yield: 60.0%

Methyl diethylphosphonoacetate (1067-74-9) → phosphonoacetic acid (4408-78-0)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1002/hc.10082

Reference yield:

trimethyl phosphonoacetate (5927-18-4) → phosphonoacetic acid (4408-78-0) + [hydroxy(methoxy)phosphinoyl]acetic acid (66448-21-3)

Guidance literature:

trimethyl phosphonoacetate; With potassium carbonate; at 20 - 30 ℃; for 15h;

In water; at 100 - 105 ℃; for 4h;

With hydrogenchloride; In water; at 90 ℃; for 6h;

DOI:10.1134/S1070363215100394

upstream raw materials:

diethyl 1-cyanomethylphosphonate

diisopropyl (methoxycarbonylmethyl)phosphonate

diethoxyphosphoryl-acetic acid ethyl ester

phosphonoacetic acid ethyl ester

Downstream raw materials:

phosphonoacetic acid ethyl ester

phosphonoacetic acid trimethyl ester

Cyclopentylideneacetic acid methyl ester

2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate

Refernces

• 1、 Al Hejami, Ahmed,Beauchemin, Diane,Evans, Alysa,Gama, Simanga R.,Hammerschmidt, Friedrich,Hupp, Kendall,McClean, Mimi,Pallitsch, Katharina,Stankovic, Toda,Zechel, David L.. "Biosynthesis of the Fungal Organophosphonate Fosfonochlorin Involves an Iron(II) and 2-(Oxo)glutarate Dependent Oxacyclase". . . Retrieved 2021/09/22.
• 2、 Alimbarova,Kharlamov,Bondarenko,Barinskii. "Composition on the basis of phosphonoacetic acid. Synthesis and antiviral activity". . p. 2441 - 2448. Retrieved 2015/11/24.