4721-17-9

Basic information

• Product Name: N-HEXADECYLPHOSPHONIC ACID
• Synonyms: N-HEXADECYLPHOSPHONIC ACID;HDPA;n-Hexadecylphosphonicacid,min.97%;n-Hexadecylphosphonic acid, min. 97%;1-Hexadecylphosphonic acid;Hexadecylphosphonic acid;Hexadecylphosphonic acid 97%;P-hexadecyl-Phosphonic acid
• CAS NO: 4721-17-9
• Molecular Formula: C16H35O3P
• Molecular Weight: 306.42
• Product Categories: organic phosphonic acid
• Mol File: 4721-17-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 96-99°C
• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 236.6 °C
• Appearance: white to off-white/Powder
• Density: 1.246 g/cm³
• Vapor Pressure: 6.46E-09mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-HEXADECYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-HEXADECYLPHOSPHONIC ACID(4721-17-9)
• EPA Substance Registry System: N-HEXADECYLPHOSPHONIC ACID(4721-17-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4721-17-9(Hazardous Substances Data)

Usage

Description

N-HEXADECYLPHOSPHONIC ACID, also known as Hexadecylphosphonic acid (HDPA), is an alkyl phosphonic acid that is utilized in the formation of self-assembled monolayers (SAMs) for the surface modification of metal oxide nanostructures. It possesses unique properties that make it suitable for various applications across different industries.

Uses

Used in Microcontact Printing:
N-HEXADECYLPHOSPHONIC ACID is used as a resist on the metal substrate for microcontact printing. This application takes advantage of its ability to form a stable and uniform layer on the metal surface, which is crucial for the accurate transfer of patterns during the printing process.
Used in Surface-Controlled Organic Transistors:
In the development of dielectric hybrids for surface-controlled organic transistors, N-HEXADECYLPHOSPHONIC ACID is used as a self-assembled monolayer (SAM). Its role in this application is to modify the surface of metal oxide nanostructures, enhancing the performance and efficiency of the transistors by providing a controlled interface between the organic and inorganic components.

InChI:InChI=1S/C18H20N2O4S/c1-4-23-16(21)14(17(22)24-5-2)10-19-18-20-15(11-25-18)13-8-6-12(3)7-9-13/h6-11H,4-5H2,1-3H3,(H,19,20)

Upstream product

• 2629-28-9 hexadecylphosphonous acid 
• 6068-28-6 tosylate de n-hexadecyle 
• 122-52-1 triethyl phosphite 
• 112-82-3 hexadecanyl bromide 
• 16165-71-2 hexadecanphosphonic acid diethyl ester 
• 629-73-2 1-Hexadecene 
• 84869-93-2 hexadecyl-phosphonic acid dibutyl ester 

Relevant articles and documents

Synthesis of Long-Chain n-Alkylphosphonic Acids by Phosphonylation of Alkyl Bromides with Red Phosphorus and Superbase under Micellar/Phase Transfer Catalysis

Long-chain n-Alkylphosphonic acids, AlkP(O)(OH)2, are synthesized in up to 91 % yield (mostly 40–60 %) by straightforward phosphonylation of alkyl bromides (AlkBr, Alk=C4–C18) with red phosphorus (Pn) in the multiphase KOH/H2O/toluene system in the presence of 2–10 mol % of cetyltrimethylammonium bromide (CTAB), acting as a micellar/phase transfer catalyst and as a generator/transporter of superbasic hydroxide anions, the intermediate potassium phosphinates being in situ oxidized/neutralized by nitric acid. The key steps of the phosphonylation mechanism are the P?P bond cleavage of Pn polymeric molecules by superbasic ?OH anions, dissolved in the CTAB micelles, and phase transfer of polyphosphide anions to the organic phase and their alkylation with AlkBr.

Synthesis and structural study of long-chain hydrocarbon alkylphosphonic acids

Long-chain dialkyl alkylphosphonates were synthesized by radical addition of dialkyl hydrogenphosphonates onto alkenes in presence of di(t-butyl) peroxide. This synthetic route leads to high yields between 94 and 97%. We performed chemical modifications of these phosphonates in order to obtain acidic derivatives. The structure of these compounds was characterized by NMR analyses and mass spectroscopy. We also studied their thermal behaviour and various crystalline phases were put in evidence by differential scanning calorimetry and optical microscopy. The thermal stability of these compounds was compared by thermogravimetric analyses.