Phosphonoacetaldehyde

Base Information

• Chemical Name: Phosphonoacetaldehyde
• CAS No.: 16051-76-6
• Molecular Formula: C2H5 O4 P
• Molecular Weight: 124.033
• Hs Code.: 2931900090
• UNII: VPZ8FR5BMZ
• DSSTox Substance ID: DTXSID60166898
• Nikkaji Number: J431.380A
• Wikidata: Q27094110
• Metabolomics Workbench ID: 51164
• Mol file: 16051-76-6.mol

Synonyms:2-phosphonoacetaldehyde;acetylphosphonate;phosphonoacetaldehyde

Chemical Property of Phosphonoacetaldehyde

Chemical Property:

• Vapor Pressure: 7.78E-06mmHg at 25°C
• Boiling Point: 350°Cat760mmHg
• Flash Point: 165.5°C
• PSA: 84.41000
• Density: 1.589g/cm³
• LogP: -0.63700
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 123.99254563
• Heavy Atom Count: 7
• Complexity: 102

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=O)P(=O)(O)O

Technology Process of Phosphonoacetaldehyde

There total 7 articles about Phosphonoacetaldehyde 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:

cesium (S)-N-(1-phenylethyl)(ethoxyvinyl)thiophosphonoamidate (143591-28-0,143591-35-9) → phosphonoacetalhdehyde (16051-76-6) + (thiophosphono)acetaldehyde (142181-54-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 25 ℃; for 3.5h; Title compound not separated from byproducts;

Reference yield:

3‐phosphopyruvate (5824-58-8) + phosphonopyruvate decarcoxylase → phosphonoacetalhdehyde (16051-76-6)

Guidance literature:

With Streptomyces wedmorensis 144-91; thiamine diphosphate; magnesium sulfate; In various solvent(s); at 30 ℃; Enzymatic reaction;

DOI:10.7164/antibiotics.50.212

Reference yield:

phospho(enol)pyruvic acid mono potassium salt (4265-07-0) → phosphonoacetalhdehyde (16051-76-6)

Guidance literature:

With Ppd-Bf-His enzyme; RhiH-N-His enzyme; thiamine diphosphate; magnesium chloride; at 30 ℃; for 0.75h; pH=7.5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.chembiol.2009.11.017

upstream raw materials:

(2-butoxy-vinyl)-phosphonic acid dichloride

(trans-2-ethoxy-vinyl)-phosphonothioic acid dichloride

cesium (S)-N-(1-phenylethyl)(ethoxyvinyl)thiophosphonoamidate

3‐phosphopyruvate

Downstream raw materials:

β-Hydroxyethanphosphonsaeure

phosphonoacetic acid

acetaldehyde

Refernces

• 1、 Nakashita, Hideo,Watanabe, Kei,Hara, Osamu,Hidaka, Tomomi. "Studies on the biosynthesis of bialaphos. Biochemical mechanism of C-P bond formation: Discovery of phosphonopyruvate decarboxylase which catalyzes the formation of phosphonoacetaldehyde from phosphonopyruvate". . p. 212 - 219. Retrieved 1997.
• 2、 Borisova, Svetlana A.,Circello, Benjamin T.,Zhang, Jun Kai,van der Donk, Wilfred A.,Metcalf, William W.. "Biosynthesis of Rhizocticins, Antifungal Phosphonate Oligopeptides Produced by Bacillus subtilis ATCC6633". supporting information; experimental part. p. 28 - 37. Retrieved 2010/07/05.