4724-47-4

Basic information

• Product Name: N-OCTADECYLPHOSPHONIC ACID
• Synonyms: octadecylphosphonic acid;N-OCTADECYLPHOSPHONIC ACID, 93+%;n-Octadecylphosphonicacid,min.97%;n-Octadecylphosphonic acid, 98 %;Octadecanephosphonic acid;n-Octadecylphosphonic acid,min. 97%;stearylphosphonic acid;1-Octadecylphosphonic acid
• CAS NO: 4724-47-4
• Molecular Formula: C₁₈H₃₉O₃P
• Molecular Weight: 334.47
• EINECS: 225-216-4
• Product Categories: API intermediates;organic phosphonic acid
• Mol File: 4724-47-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 99℃
• Boiling Point: 463.6 °C at 760 mmHg
• Flash Point: 234.2 °C
• Appearance: White to off-white/Crystalline
• Density: 0.969
• Vapor Pressure: 7.02E-10mmHg at 25°C
• Refractive Index: 1.465
• PKA: 2?+-.0.10(Predicted)
• Water Solubility: Insoluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N-OCTADECYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-OCTADECYLPHOSPHONIC ACID(4724-47-4)
• EPA Substance Registry System: N-OCTADECYLPHOSPHONIC ACID(4724-47-4)

Safety Data

• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4724-47-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4724-47-4 differently. You can refer to the following data:
1. 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.
2. 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.

Chemical Properties

crystalline solid

General Description

Octadecylphosphonic acid (OPA) is used as a self-assembled monolayer that forms a surfactant which strongly bonds with the surface atoms of different metal oxides. It provides hydrophobic properties and covers a higher surface area than the predominantly used silanes.

InChI:InChI=1/C18H39O3P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(19,20)21/h2-18H2,1H3,(H2,19,20,21)

Synthetic route

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

Conditions	Yield
Stage #1: 1-Bromooctadecane With phosphoric acid; N,O-Bis(trimethylsilyl)trifluoroacetamide at 120℃; Stage #2: With water In methanol at 20℃; for 2h; Further stages.;	99%
Stage #1: 1-Bromooctadecane With potassium hydroxide semihydrate; phosphorus; cetyltrimethylammonim bromide In water; toluene at 70℃; for 6h; Inert atmosphere; Stage #2: With nitric acid In water at 100 - 110℃; for 2h; pH=4; Inert atmosphere;	20%
Multi-step reaction with 2 steps 1: hexane 2: concentrated aqueous HCl View Scheme
Multi-step reaction with 2 steps 1.1: 150 °C / Inert atmosphere; Schlenk technique 2.1: trimethylsilyl bromide / dichloromethane 2.2: 3 h View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide 2: trimethylsilyl bromide View Scheme

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

Conditions	Yield
Stage #1: octadecylphosphonate de diethyle With trimethylsilyl bromide In dichloromethane Stage #2: With methanol for 3h;	70%
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 20 °C 2: MeOH / CH2Cl2 / 1 h View Scheme
Stage #1: octadecylphosphonate de diethyle With trimethylsilyl bromide Stage #2: In methanol

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

Conditions	Yield
With hydrogenchloride

stearylphosphonic chloride (3220-51-7) → n-octadecylphosphonic acid (4724-47-4)

Conditions	Yield
With acetic acid

O,O'-bis(trimethylsilyl)octadecylphosphonic acid (81302-75-2) → n-octadecylphosphonic acid (4724-47-4)

Conditions	Yield
With methanol In dichloromethane for 1h;

octadec-1-ene (112-88-9) → n-octadecylphosphonic acid (4724-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / (tBuO)2 / 6 h / 135 °C 2: CH2Cl2 / 2 h / 20 °C 3: MeOH / CH2Cl2 / 1 h View Scheme

1-octadecanol (112-92-5) → n-octadecylphosphonic acid (4724-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: carbon tetrabromide; triphenylphosphine / dichloromethane 2: sodium hydride / N,N-dimethyl-formamide 3: trimethylsilyl bromide View Scheme

n-octadecylphosphonic acid (4724-47-4) + copper diacetate (142-71-2) → Cu(2+)*CH3(CH2)17PO3(2-)=Cu(CH3(CH2)17PO3)

Conditions	Yield
In ethanol; water aq. soln. of CuCl2 added dropwise to soln. of acid in H2O/EtOH (3/1, v/v) (1:1 molar ratio), mixt. stirred overnight at 70°C; filtered off, washed (H2O, EtOH), dried at room temp.;	94.2%

ferrous(II) sulfate heptahydrate + n-octadecylphosphonic acid (4724-47-4) → Fe(octadecylphosphonate)(H2O) (879868-29-8)

Conditions	Yield
With NH2CONH2 In ethanol; water under N2 atm. using Schlenk techniques; mixt. of FeSO4*7H2O, octadecylphosphonic acid, NH2CONH2 placed in ampoule purged with N2 prior addition of degassed EtOH/H2O; ampoule sealed off under vac.; heated at 80°C for a few ds; cooled; powder collected; washed (H2O); final pH of filtrate was around 7.1; elem. anal.;	90%

n-octadecylphosphonic acid (4724-47-4) + salicylic alcohol (90-01-7) → 2-stearyl-4H-1,3,2-benzodioxaphosphorin 2-oxide

Conditions	Yield
Stage #1: n-octadecylphosphonic acid With phosphorus pentachloride; trichlorophosphate at 120℃; for 2h; Stage #2: salicylic alcohol With pyridine; dmap In tetrahydrofuran at 20℃; for 48h; Further stages.;	23%

n-octadecylphosphonic acid (4724-47-4) → octadecyl-phosphonic acid monomethyl ester (25371-55-5)

Conditions	Yield
With phosphorus pentachloride beim anschliessenden Behandeln mit Methanol und Pyridin;

n-octadecylphosphonic acid (4724-47-4) + cytidine 5'-monophosphomorpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt (76742-18-2) → cytidine-5'-octadecylphosphonophosphate

Conditions	Yield
With pyridine at 25 - 35℃; for 80h;

n-octadecylphosphonic acid (4724-47-4) + tributylphosphane telluride (2935-46-8) + cadmium(II) oxide → cadmium telluride

Conditions	Yield
With octadecene (ODE) In further solvent(s) mixt. of CdO, octadecylphosphonic acid, octadecene heated to 300°C; cooled to room temp.; telluride deriv. added; mixt. degassed; under Ar flow soln. stirred and heated to 240°C (25 K/min);

cobalt(II) chloride hexahydrate + n-octadecylphosphonic acid (4724-47-4) → cobalt octadecylphosphonate monohydrate

Conditions	Yield
With HCl or KOH org. compd. spreading onto subphase of Co-compd. on Si wafer substrate (pH of subpase maintaining at 5.5-5.8 using HCl or KOH); XRD;

manganese(II) chloride tetrahydrate + n-octadecylphosphonic acid (4724-47-4) → manganese octadecylphosphonate monohydrate

Conditions	Yield
In water formation of monolayer on spreading phosphonic acid onto aq. MnCl2 (pH 5.2-5.7); compresing into multilayers at 17 mN/m onto calcium arachidate substrate;

nickel(II) chloride hexahydrate + n-octadecylphosphonic acid (4724-47-4) + water (7732-18-5) → nickel(II) octadecylphosphonate hydrate (556010-94-7)

Conditions	Yield
With urea In water a soln. of Ni salt added to a soln. of acid and urea, refluxed for a wk at 80°C; ppt. filtered, washed (water, methanol), dried (air); elem. anal.;

iron(II) chloride hexahydrate + n-octadecylphosphonic acid (4724-47-4) → Fe(octadecylphosphonate)(H2O) (879868-29-8)

Conditions	Yield
With NH2CONH2 In water under N2 atm. using Schlenk techniques;

n-octadecylphosphonic acid (4724-47-4) + cadmium(II) oxide → cadmium n-octadecylphosphonate

Conditions	Yield
With cyanex-921 the mixt. of (C8H17)3PO, n-octadecylphosphonic acid and CdO was degassedat 120°C and 200-400 mTorr for 60 min, filled Ar, CdO was dissol ved at 320°C, 150-180°C, 300 mTorr; detected by NMR spectra in CDCl3;
With cyanex-921 at 150 - 300℃; Schlenk technique; Inert atmosphere;
With cyanex-921 at 120 - 290℃; Inert atmosphere; Schlenk technique;

tellurium + n-octadecylphosphonic acid (4724-47-4) + cadmium(II) oxide → cadmium telluride

Conditions	Yield
With TOP In neat (no solvent) mixt. CdO, n-octadecylphosphonic acid and trioctylphosphine oxide was inserted into preheated (300-330°C) bath and equilibrated for several minutes, soln. prepared from Te and trioctylphosphine at 240°Cand Bi nanoparticleswas was added;

n-octadecylphosphonic acid (4724-47-4) + bis(trimethylsilyl)selenide (4099-46-1) → C21H47O3PSi + O,O'-bis(trimethylsilyl)octadecylphosphonic acid (81302-75-2)

Conditions	Yield
In d8-toluene Heating;

n-octadecylphosphonic acid (4724-47-4) + bis(trimethylsilyl)selenide (4099-46-1) → O,O'-bis(trimethylsilyl)octadecylphosphonic acid (81302-75-2)

Conditions	Yield
In d8-toluene Heating;

n-octadecylphosphonic acid (4724-47-4) → potassium octadecylphosphonate

Conditions	Yield
With potassium hydroxide In water at 60℃;
With KOH In water

n-octadecylphosphonic acid (4724-47-4) → potassium hydrogenoctadecylphosphonate (19035-78-0)

Conditions	Yield
With potassium hydroxide In water at 60℃;

dimethyl-n-octylchlorosilane (18162-84-0) + n-octadecylphosphonic acid (4724-47-4) → octadecylphosphonate dimethyloctylsilyl ester

Conditions	Yield
for 8h; Heating;

n-octadecylphosphonic acid (4724-47-4) + Se*C12H27P + cadmium(II) oxide → [Cd2Se(ODPA)n]m

Conditions	Yield
Stage #1: n-octadecylphosphonic acid; cadmium(II) oxide With cyanex-921 at 130℃; for 1h; Stage #2: at 310 - 350℃; Inert atmosphere; Stage #3: Se*C12H27P Further stages;

Upstream product

• 112-92-5 1-octadecanol 
• 16165-72-3 octadecylphosphonate de diethyle 
• 112-88-9 octadec-1-ene 
• 81302-75-2 O,O'-bis(trimethylsilyl)octadecylphosphonic acid 
• 112-89-0 1-Bromooctadecane 
• 3220-51-7 stearylphosphonic chloride 
• 52235-56-0 octadecyl-phosphonic acid dibutyl ester 

Downstream Products

• 25371-55-5 octadecyl-phosphonic acid monomethyl ester 

Relevant articles and documents

Novel synthesis of [33P]-(2-chloroethyl)phosphonic acid.

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Synthesis of Phosphonic Acid Ligands for Nanocrystal Surface Functionalization and Solution Processed Memristors

Here, we synthesized 2-ethylhexyl, 2-hexyldecyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, oleyl, and n-octadecyl phosphonic acid and used them to functionalize CdSe and HfO2 nanocrystals. In contrast to branched carboxylic acids, postsynthetic surface functionalization of CdSe and HfO2 nanocrystals was readily achieved with branched phosphonic acids. Phosphonic acid capped HfO2 nanocrystals were subsequently evaluated as memristors using conductive atomic force microscopy. We found that 2-ethylhexyl phosphonic acid is a superior ligand, combining a high colloidal stability with a compact ligand shell that results in a record-low operating voltage that is promising for application in flexible electronics.

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.