Hexadecylphosphonic acid

Base Information

• Chemical Name: Hexadecylphosphonic acid
• CAS No.: 4721-17-9
• Molecular Formula: C₁₆H₃₅O₃P
• Molecular Weight: 306.426
• European Community (EC) Number: 811-098-7
• DSSTox Substance ID: DTXSID20549385
• Nikkaji Number: J813.442A
• Wikidata: Q82428420
• Mol file: 4721-17-9.mol

Synonyms:Hexadecylphosphonic acid;4721-17-9;n-Hexadecylphosphonic acid;N-HEXADECYLPHOSPHONICACID;cetylphosphonic acid;MFCD00015836;SCHEMBL33472;Hexadecylphosphonic acid, 97%;DTXSID20549385;AKOS017343250;CS-0361632;H1488;T72502

Chemical Property of Hexadecylphosphonic acid

Chemical Property:

• Vapor Pressure: 6.46E-09mmHg at 25°C
• Melting Point: 96-99°C
• Refractive Index: 1.59
• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 236.6 °C
• PSA: 67.34000
• Density: 1.246 g/cm³
• LogP: 5.64540
• Storage Temp.: 2-8°C
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 306.23238197
• Heavy Atom Count: 20
• Complexity: 238

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hexadecylphosphonic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCP(=O)(O)O
• Uses: HDPA forms a resist on the metal substrate which may be used for microcontact printing. It may also find usage as a SAM for the development of a dielectric hybrid for surface controlled organic transistors.

Technology Process of Hexadecylphosphonic acid

There total 8 articles about Hexadecylphosphonic 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: 97.0%

hexadecylphosphonous acid (2629-28-9) → hexadecylphosphonic acid (4721-17-9)

Guidance literature:

With dihydrogen peroxide; In water; for 6h;

Reference yield: 42.0%

hexadecanyl bromide (112-82-3) → hexadecylphosphonic acid (4721-17-9)

Guidance literature:

hexadecanyl bromide; With potassium hydroxide semihydrate; phosphorus; cetyltrimethylammonim bromide; In water; toluene; at 90 - 95 ℃; for 6h; Inert atmosphere;

With nitric acid; In water; at 100 - 110 ℃; for 2h; pH=4; Inert atmosphere;

DOI:10.1002/ejoc.202100067

Reference yield:

silica-gel + tosylate de n-hexadecyle (6068-28-6,53012-52-5) + triethyl phosphite (122-52-1) → hexadecylphosphonic acid (4721-17-9)

Guidance literature:

With hydrogenchloride; sodium; In tetrahydrofuran; water;

upstream raw materials:

hexadecyl-phosphonic acid dibutyl ester

1-Hexadecene

hexadecanphosphonic acid diethyl ester

hexadecanyl bromide