Dioleyl phosphonate

Base Information

• Chemical Name: Dioleyl phosphonate
• CAS No.: 25088-57-7
• Molecular Formula: C36H71 O3 P
• Molecular Weight: 582.932
• European Community (EC) Number: 246-608-1
• UNII: U281PT9Z72
• DSSTox Substance ID: DTXSID801021087
• Mol file: 25088-57-7.mol

Synonyms:Dioleyl phosphonate;U281PT9Z72;Phosphonic acid, di-(9Z)-9-octadecenyl ester;25088-57-7;Dioleyl phosphite;PHOSLEX H 18D;CHELEX H 18D;SCHEMBL305442;UNII-U281PT9Z72;JP 218OR;DIOLEYL PHOSPHITE [HSDB];HSDB 2602;HBUROESZWYWHFQ-CLFAGFIQSA-N;DTXSID801021087;EINECS 246-608-1;DI-9-OCTADECENYL PHOSPHONATE, (Z,Z)-;Phosphonic acid, di-9-octadecenyl ester (Z,Z)-;Phosphonic acid, di-9-octadecenyl ester, (Z,Z)-;9-OCTADECEN-1-OL, PHOSPHONATE (2:1), (Z,Z)-

Chemical Property of Dioleyl phosphonate

Chemical Property:

• Vapor Pressure: 1.03E-18mmHg at 25°C
• Boiling Point: 652.6°C at 760 mmHg
• Flash Point: 348.5°C
• XLogP3: 15.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 34
• Exact Mass: 581.50625809
• Heavy Atom Count: 40
• Complexity: 500

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCCO[P+](=O)OCCCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCO[P+](=O)OCCCCCCCC/C=C\CCCCCCCC

Technology Process of Dioleyl phosphonate

There total 2 articles about Dioleyl 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: 75.0%

oleoyl alcohol (143-28-2,593-47-5,84286-21-5) → diolelyl hydrogen phosphonate (25088-57-7)

Guidance literature:

With pyridine; phosphorus trichloride; In dichloromethane;

DOI:10.1055/s-2003-38074

Reference yield: 65.2%

oleoyl alcohol (143-28-2,593-47-5,84286-21-5) + diphenyl hydrogen phosphite (4712-55-4) → diolelyl hydrogen phosphonate (25088-57-7)

Guidance literature:

With pyridine; at 65 ℃; for 3h;

Reference yield:

diolelyl hydrogen phosphonate (25088-57-7) → dioleyl phosphate (14450-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; i-Pr₂NEt / 20 °C

2: Et₃N; i-Pr₂NEt / CH₂Cl₂

3: 0.72 g / H₂O / 0.5 h / pH 4 - 5 / Acid hydrolysis

With water; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1055/s-2003-38074

upstream raw materials:

oleoyl alcohol

diphenyl hydrogen phosphite

Downstream raw materials:

dioleyl phosphate

Refernces

• 1、 Berchel, Mathieu,Hocquigny, Alexis,Jaffrès, Paul-Alain,Khalil, Montassar,Montier, Tristan. "Phosphonodithioester–amine coupling as a key reaction step for the design of cationic amphiphiles used for gene delivery". . . Retrieved 2021/12/24.
• 2、 Kuiper, Johanna M.,Hulst, Ron,Engberts, Jan B. F. N.. "A selective and mild synthetic route to dialkyl phosphates". . p. 695 - 698. Retrieved 2007/10/03.