Dibutylphosphine oxide

Base Information

• Chemical Name: Dibutylphosphine oxide
• CAS No.: 15754-54-8
• Molecular Formula: C8H19OP
• Molecular Weight: 162.212
• DSSTox Substance ID: DTXSID80422862
• Wikidata: Q72465311
• Mol file: 15754-54-8.mol

Synonyms:dibutylphosphine oxide;dibutyl(oxo)phosphanium;15754-54-8;Phosphine oxide, dibutyl-;di-n-butylphosphine oxide;1-(butylphosphonoyl)butane;1-butyl-phosphonoyl-butane;di(n-butyl)phosphine oxide;SCHEMBL304754;DTXSID80422862;CSILLBGWWDXKNC-UHFFFAOYSA-N;AKOS006280819;AT34650;FT-0755604

Chemical Property of Dibutylphosphine oxide

Chemical Property:

• Melting Point: 55-58℃
• Boiling Point: 224℃
• Flash Point: 89℃
• PSA: 40.54000
• LogP: 3.14630
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 161.109527191
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[P+](=O)CCCC

Technology Process of Dibutylphosphine oxide

There total 14 articles about Dibutylphosphine oxide 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: 90.0%

butyl magnesium bromide (693-04-9) + phosphonic acid diethyl ester (762-04-9) → dibutylphosphine oxide (15754-54-8)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0517832

Reference yield: 87.0%

n-butyllithium (109-72-8,29786-93-4) + phosphonic acid diethyl ester (762-04-9) → dibutylphosphine oxide (15754-54-8)

Guidance literature:

In tetrahydrofuran; at 0 - 23 ℃; for 0.75h;

DOI:10.1039/c4cc06851c

Reference yield: 65.0%

n-Butyl chloride (109-69-3) + phosphonic acid diethyl ester (762-04-9) → dibutylphosphine oxide (15754-54-8)

Guidance literature:

With magnesium; In diethyl ether; at 0 - 26 ℃; for 1.5h;

DOI:10.1039/c4ra03292f

upstream raw materials:

ethyl ester of dibutyl phosphinic acid

1-bromo-butane

dibutylphosphinous iodide

butyl magnesium bromide

Downstream raw materials:

dibutyl-(2,2,2-trichloro-1-hydroxy-ethyl)-phosphine oxide

α-Cyanobenzyl-dibutylphosphinat

trimethylsilyl dibutylphosphinite

Dibutylphosphinyl-diphenyl-methanol

Refernces

• 1、 Gusarova, Nina K.,Sutyrina, Anastasiya O.,Kuimov, Vladimir A.,Malysheva, Svetlana F.,Belogorlova, Natalia A.,Volkov, Pavel A.,Trofimov, Boris A.. "Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides". . p. 328 - 330. Retrieved 2019/06/13.
• 2、 Keglevich, Gyoergy,Jablonkai, Erzsebet,Balazs, Laszlo B.. "A "green" variation of the Hirao reaction: The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions". . p. 22808 - 22816. Retrieved 2014/06/23.