4-Hydroxy-3-oxobutyl-1-phosphonic acid

Base Information

• Chemical Name: 4-Hydroxy-3-oxobutyl-1-phosphonic acid
• CAS No.: 51827-90-8
• Molecular Formula: C₄H₉O₅P
• Molecular Weight: 168.086
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40199785
• Nikkaji Number: J679.406H
• Wikidata: Q83072763
• Mol file: 51827-90-8.mol

Synonyms:4-hydroxy-3-oxobutyl-1-phosphonic acid;4-hydroxy-3-oxobutyl-1-phosphonic acid, sodium salt;DHAP-M

Chemical Property of 4-Hydroxy-3-oxobutyl-1-phosphonic acid

Chemical Property:

• Vapor Pressure: 1.73E-09mmHg at 25°C
• Boiling Point: 437.4°Cat760mmHg
• Flash Point: 218.4°C
• PSA: 104.64000
• Density: 1.551g/cm³
• LogP: -0.88440
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 168.01876038
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CP(=O)(O)O)C(=O)CO

Technology Process of 4-Hydroxy-3-oxobutyl-1-phosphonic acid

There total 4 articles about 4-Hydroxy-3-oxobutyl-1-phosphonic 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: 92.0%

3-oxo-4-(2,2-dimethylpropionyl)oxybutylphosphonic acid diisopropyl ester → 4-hydroxy-3-oxobutylphosphonic acid (51827-90-8)

Guidance literature:

With hydrogenchloride; In water; for 3h; Heating;

DOI:10.1016/S0008-6215(97)10026-X

Reference yield: 91.0%

diethyl 3-oxo-4-hydroxybutyl-1-phosphonate (56119-69-8) → 4-hydroxy-3-oxobutylphosphonic acid (51827-90-8)

Guidance literature:

With trimethylsilyl bromide; water; at -20 ℃;

DOI:10.1016/0040-4039(95)01678-B

Reference yield:

1-acetoxybut-3-en-2-one (38982-28-4) + triethyl phosphite (122-52-1) → 4-hydroxy-3-oxobutylphosphonic acid (51827-90-8)

Guidance literature:

Multistep reaction; (i) EtOH, (ii) aq. HCl;

DOI:10.1021/jm00249a026

upstream raw materials:

1-acetoxybut-3-en-2-one

triethyl phosphite

(S)-3,4-Dihydroxybutylphosphonic acid

diethyl 3-oxo-4-hydroxybutyl-1-phosphonate

Refernces

• 1、 Arth, Hans-Lothar,Fessner, Wolf-Dieter. "Practical synthesis of 4-hydroxy-3-oxobutylphosphonic acid and its evaluation as a bio-isosteric substrate of DHAP aldolase". . p. 313 - 321. Retrieved 2007/10/03.