Dibutyl (1-hydroxybutyl)phosphonate

Base Information

• Chemical Name: Dibutyl (1-hydroxybutyl)phosphonate
• CAS No.: 23054-89-9
• Molecular Formula: C₁₂H₂₇O₄P
• Molecular Weight: 266.318
• NSC Number: 191875
• DSSTox Substance ID: DTXSID90307515
• Mol file: 23054-89-9.mol

Synonyms:(1-hydroxy-butyl)-phosphonic acid dibutyl ester;23054-89-9;NSC191875;DTXSID90307515;dibutyl (1-hydroxybutyl)phosphonate;NSC-191875

Chemical Property of Dibutyl (1-hydroxybutyl)phosphonate

Chemical Property:

• Vapor Pressure: 2.66E-06mmHg at 25°C
• Boiling Point: 350.3°C at 760 mmHg
• Flash Point: 165.6°C
• Density: 1.018g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 266.16469634
• Heavy Atom Count: 17
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCOP(=O)(C(CCC)O)OCCCC

Technology Process of Dibutyl (1-hydroxybutyl)phosphonate

There total 3 articles about Dibutyl (1-hydroxybutyl)phosphonate 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: 55.0%

phosphoric acid tributyl ester (126-73-8) → dibutyl 1-hydroxybutylphosphonate (23054-89-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 3h;

DOI:10.1007/BF00807567

Reference yield:

dibutyl hydrogen phosphite (1809-19-4) + butyraldehyde (123-72-8) → dibutyl 1-hydroxybutylphosphonate (23054-89-9)

Guidance literature:

With sodium methylate;

Reference yield:

tri-n-butyl phosphite (102-85-2) → dibutyl 1-hydroxybutylphosphonate (23054-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water / tetrahydrofuran / 12 h / Inert atmosphere; Reflux

2.1: triethylamine; iron(III) chloride / tetrahydrofuran / 0.25 h

2.2: 24 h

With iron(III) chloride; water; triethylamine; In tetrahydrofuran;

DOI:10.1002/adsc.201300653

upstream raw materials:

dibutyl hydrogen phosphite

butyraldehyde

phosphoric acid tributyl ester

tri-n-butyl phosphite