Octadecylphosphonic acid

Base Information

• Chemical Name: Octadecylphosphonic acid
• CAS No.: 4724-47-4
• Molecular Formula: C18H39O3P
• Molecular Weight: 334.48
• Hs Code.: 29319090
• European Community (EC) Number: 225-216-4
• UNII: KDX6MSF5PN
• DSSTox Substance ID: DTXSID5063574
• Nikkaji Number: J262.409E
• Wikipedia: Octadecylphosphonic_acid
• Wikidata: Q7076691
• ChEMBL ID: CHEMBL190741
• Mol file: 4724-47-4.mol

Synonyms:Octadecylphosphonic acid;4724-47-4;n-octadecylphosphonic acid;Phosphonic acid, octadecyl-;octadecyl phosphonic acid;KDX6MSF5PN;Phosphonic acid, P-octadecyl-;EINECS 225-216-4;C18H39O3P;stearylphosphonic acid;UNII-KDX6MSF5PN;Octadecyl-phosphonic acid;P-Octadecylphosphonic acid;1-Octadecanephosphonic acid;SCHEMBL107866;Octadecylphosphonic acid, 97%;CHEMBL190741;DTXSID5063574;Octadecylphosphonic acid, >=99%;GEO-04391;MFCD00015838;AKOS005137958;CS-W011929;AS-58371;FT-0733675;O0371;EN300-7396599;Q7076691;Z3225836453;6E0

Chemical Property of Octadecylphosphonic acid

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 7.02E-10mmHg at 25°C
• Melting Point: 99℃
• Refractive Index: 1.465
• Boiling Point: 463.6 °C at 760 mmHg
• PKA: 2?+-.0.10(Predicted)
• Flash Point: 234.2 °C
• PSA: 67.34000
• Density: 0.969 g/cm³
• LogP: 6.42560
• Water Solubility.: Insoluble in water.
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 334.26368210
• Heavy Atom Count: 22
• Complexity: 263

Purity/Quality:

99.0% Min ^*data from raw suppliers

Octadecylphosphonic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCP(=O)(O)O
• Uses: Octadecylphosphonic acid is used as detergents, dispersants, emulsifiers, and chelating agents. Alkyl phosphonic acids are typically sparingly soluble in both organic solvents and water, but become more soluble in water when neutralized to phosphonates at neutral to high pH. n-Octadecylphosphonic acid is used in thermal paper for receipts, adding machines and tickets. It acts as surfactant, emulsifier, dispersants and chelating agents. Further, it is a long chain phosphonic acid compound utilized for proteomics research. In addition to this, it is used to prepare modified mesoporous magnetic nano particles through Lewis acid/base interaction.

Technology Process of Octadecylphosphonic acid

There total 8 articles about Octadecylphosphonic 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: 99.0%

1-Bromooctadecane (112-89-0) → n-octadecylphosphonic acid (4724-47-4)

Guidance literature:

1-Bromooctadecane; With phosphoric acid; N,O-Bis(trimethylsilyl)trifluoroacetamide; at 120 ℃;

With water; In methanol; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jo0013608

Reference yield: 70.0%

octadecylphosphonate de diethyle (16165-72-3) → n-octadecylphosphonic acid (4724-47-4)

Guidance literature:

octadecylphosphonate de diethyle; With trimethylsilyl bromide; In dichloromethane;

With methanol; for 3h;

DOI:10.4314/bcse.v28i1.17

Reference yield:

octadecyl-phosphonic acid dibutyl ester (52235-56-0) → n-octadecylphosphonic acid (4724-47-4)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01223a046

upstream raw materials:

octadecyl-phosphonic acid dibutyl ester

stearylphosphonic chloride

1-Bromooctadecane

O,O'-bis(trimethylsilyl)octadecylphosphonic acid

Downstream raw materials:

octadecyl-phosphonic acid monomethyl ester

Refernces

• 1、 Kuimov, Vladimir A.,Malysheva, Svetlana F.,Belogorlova, Natalia A.,Albanov, Alexander I.,Gusarova, Nina K.,Trofimov, Boris A.. "Synthesis of Long-Chain n-Alkylphosphonic Acids by Phosphonylation of Alkyl Bromides with Red Phosphorus and Superbase under Micellar/Phase Transfer Catalysis". supporting information. p. 1596 - 1602. Retrieved 2021/03/03.
• 2、 Mungalimane, Amshumali. "High yield synthesis of some phosphonic acid derivatives as surface tethers for energy harvesting technologies". . p. 143 - 148. Retrieved 2014/03/21.