4721-24-8

Basic information

• Product Name: N-HEXYLPHOSPHONIC ACID
• Synonyms: N-HEXYLPHOSPHONIC ACID;LABOTEST-BB LT00408920;n-Hexylphosphonicacid,min.97%;n-Hexylphosphonic acid, ,min. 97%;1-Hexylphosphonic acid;n-Hexylphosphonic acid SynonyMs Hexanephosphonic acid;Hexanephosphonic acid;NSC 222656
• CAS NO: 4721-24-8
• Molecular Formula: C₆H₁₅O₃P
• Molecular Weight: 166.16
• Product Categories: organic phosphonic acid
• Mol File: 4721-24-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 108-110°C
• Boiling Point: 299.7 °C at 760 mmHg
• Flash Point: 135 °C
• Appearance: White to off-white/Powder
• Density: 1.132 g/cm³
• Vapor Pressure: 0.000278mmHg at 25°C
• Solubility: soluble in Methanol
• PKA: 2.66±0.10(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: N-HEXYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-HEXYLPHOSPHONIC ACID(4721-24-8)
• EPA Substance Registry System: N-HEXYLPHOSPHONIC ACID(4721-24-8)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R22:; R34:; R43:; R48/22:
• Safety Statements: S1/2:; S22:; S26:; S36/37/39:; S45:
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4721-24-8(Hazardous Substances Data)

Usage

Uses

n-Hexylphosphonic acid is used in the manufacturing of nanoparticles such as quantum dots, nano-metals and nano-ceramics. It is also used for coating of many materials, including nanoparticles by condensed hydrophobic monolayers.

General Description

Hexylphosphonic acid(HPA) is a phosphonic acid derivative that can be used as a capping agent and a surfactant.

InChI:InChI=1/C6H15O3P/c1-2-3-4-5-6-10(7,8)9/h2-6H2,1H3,(H2,7,8,9)/p-2

Synthetic route

diethyl hexylphosphonate (16165-66-5) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
With trimethylsilyl bromide In methanol; dichloromethane at 20℃; Inert atmosphere;	100%

1-bromo-hexane (111-25-1) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Stage #1: 1-bromo-hexane With potassium hydroxide semihydrate; phosphorus; cetyltrimethylammonim bromide In water; toluene at 85 - 90℃; for 6h; Inert atmosphere; Stage #2: With nitric acid In water at 100 - 110℃; for 2h; pH=4; Inert atmosphere;	61%
Multi-step reaction with 2 steps 1: heptane 2: concentrated aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: 15 h / 150 °C / Inert atmosphere 2: trimethylsilyl bromide / dichloromethane; methanol / 20 °C / Inert atmosphere View Scheme

dibutyl hexylphosphonate (5929-66-8) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
With hydrogenchloride

1-hexene (592-41-6) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
With phosphonic Acid; dibenzoyl peroxide

hexylphosphonic acid dichloride (928-64-3) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
With water

Hexyl-phosphonsaeure-dimethylester (6172-92-5) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
With hydrogenchloride

hexane (110-54-3) + tantalum oxide → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3, O2 2: H2O View Scheme

Dimethyl-1-hexenylphosphonat (23897-48-5) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: aq. HCl View Scheme

Dimethyl-1-diazohexan-phosphonat (26579-98-6) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: Cu / benzene 2: H2 / Pd-C / ethanol 3: aq. HCl View Scheme

C15H25N2O5PS (26584-01-0) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. Na2CO3 / diethyl ether 2: Cu / benzene 3: H2 / Pd-C / ethanol 4: aq. HCl View Scheme

1-hexene (592-41-6) + oxygen → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 19 h / 33 °C / (γ-irradiation) 2: aq. HCl View Scheme

1-bromo-hexane (111-25-1) + triethyl phosphite (122-52-1) → n-hexylphosphonic acid (4721-24-8)

Conditions	Yield
Stage #1: 1-bromo-hexane; triethyl phosphite at 150℃; for 5h; Large scale; Stage #2: With hydrogenchloride In water at 60℃; for 10h; Large scale;	170 kg

n-hexylphosphonic acid (4721-24-8) + vanadia → V(6+)*O(2-)*C6H13(1-)*PO3(3-)*H2O*C6H5CH2OH=VO(C6H13PO3)*H2O*C6H5CH2OH

Conditions	Yield
With HCl; benzyl alcohol In benzyl alcohol V2O5 is added to a soln. of (C6H13)PO(OH)2 with mineral acid, while stirring and heating at 85°C for 6 h the orange suspension becomes green, blue as the rect. proceeds (without minaral acid the react. takes 3-14 days).; Isolated by filtration, washed with ether, dried under a N2 stream, elem. anal.;	95%

n-hexylphosphonic acid (4721-24-8) + zirconyl dichloride hydrate (68254-68-2) → zirconium n-hexylphosphonate

Conditions	Yield
With hydrofluoric acid In propan-1-ol; water N2, Zr compd. dissolved in water with HF, a soln. of P compd. (H2O/1-propanol) added dropwise, HF added, refluxed 90-100°C for 5-7 d; ppt. washed (H2O, i-propanol, acetone, diethyl ether), dried (110°C, 24 h); elem. anal.;	87%

n-hexylphosphonic acid (4721-24-8) → 2,4,6-trihexyl-[1,3,5,2,4,6]-trioxatriphosphinane 2,4,6-trioxide

Conditions	Yield
Stage #1: n-hexylphosphonic acid With acetic anhydride for 2h; Heating / reflux; Stage #2: at 350℃; under 0.0750075 - 75.0075 Torr;	75%

n-hexylphosphonic acid (4721-24-8) + [Y2III(O2CtBu)6(HO2CtBu)6] + [Ni(μ-H2O)(OOCCMe3)2(HOOCCMe3)2]2 + acetonitrile (75-05-8) → [Ni6Y6(μ3-OH)2(μ2-OAc)2(O3P(n-hexyl))6(O2CtBu)16]

Conditions	Yield
With triethylamine at 150℃; for 12h; Autoclave;	49%

n-hexylphosphonic acid (4721-24-8) + [GdIII2 (O2CtBu)6(HO2CtBu)6] + [Ni(μ-H2O)(OOCCMe3)2(HOOCCMe3)2]2 + acetonitrile (75-05-8) → [Ni6Gd6(μ3-OH)2(μ2-OAc)2(O3P(n-hexyl))6(O2CtBu)16]

Conditions	Yield
With triethylamine at 150℃; for 12h; Autoclave;	46%

n-hexylphosphonic acid (4721-24-8) + dicyclohexyl-carbodiimide (538-75-0) → n-hexylphosphonic acid anhydride (72493-38-0)

Conditions	Yield
With diethyl ether

n-hexylphosphonic acid (4721-24-8) → 1-hexene (592-41-6) + hexane (110-54-3)

Conditions	Yield
With Escherichia coli RB 791 In water Product distribution; degradation and detoxification by cleavage of the carbon to phosphorus bond, and degradation by reaction of lead tetraacetate;

n-hexylphosphonic acid (4721-24-8) + dibutylstannane (1002-53-5) → {(C4H9)2SnOP(O)C6H13O}n

Conditions	Yield
In cyclohexane boiling on reflux;;
In cyclohexane boiling on reflux;;
In cyclohexane boiling on reflux;;

n-hexylphosphonic acid (4721-24-8) + water (7732-18-5) + copper dichloride → Cu(2+)*CH3(CH2)5PO3(2-)*H2O=Cu(CH3(CH2)5PO3)*H2O

Conditions	Yield
With KOH In water aq. soln. of CuCl2 added dropwise to aq. soln. of acid and KOH (1.07:0.82:1.64 molar ratio), mixt. stirred overnight at room temp.; filtered off, washed (H2O, EtOH), dried at room temp.;

zirconyl propionate + n-hexylphosphonic acid (4721-24-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.7(hexylphosphonate)0.3*(x)H2O

Conditions	Yield
Stage #1: zirconyl propionate; phosphoric acid In propan-1-ol at 20℃; Stage #2: n-hexylphosphonic acid In propan-1-ol at 20℃; for 72h;

zirconyl propionate + n-hexylphosphonic acid (4721-24-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.46(hexylphosphonate)0.54*(x)H2O

Conditions	Yield
Stage #1: zirconyl propionate; phosphoric acid In propan-1-ol at 20℃; Stage #2: n-hexylphosphonic acid In propan-1-ol at 20℃; for 72h;

zirconyl propionate + n-hexylphosphonic acid (4721-24-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.13(hexylphosphonate)0.87*(x)H2O

Conditions	Yield
Stage #1: zirconyl propionate; phosphoric acid In propan-1-ol at 20℃; Stage #2: n-hexylphosphonic acid In propan-1-ol at 20℃; for 72h;

n-hexylphosphonic acid (4721-24-8) + [GdIII2 (O2CtBu)6(HO2CtBu)6] + 3Fe(3+)*O(2-)*7C5H9O2(1-)*3C5H10O2 → 6Fe(3+)*6Gd(3+)*2O(2-)*18C5H9O2(1-)*CO3(2-)*6C6H13O3P(2-)

Conditions	Yield
Stage #1: n-hexylphosphonic acid; [GdIII2 (O2CtBu)6(HO2CtBu)6]; 3Fe(3+)*O(2-)*7C5H9O2(1-)*3C5H10O2 With triethylamine In acetonitrile at 20℃; for 0.0833333h; Stage #2: In acetonitrile at 150℃; for 12h; Autoclave;

n-hexylphosphonic acid (4721-24-8) + C56H58N2O12 → C56H58N2O12*C6H15O3P

Conditions	Yield
In chloroform-d1 at 24.84℃;

n-hexylphosphonic acid (4721-24-8) + cyanostar → 2C65H65N5*2C6H14O3P(1-)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In dichloromethane-d2 at 24.84℃;

Upstream product

• 5929-66-8 dibutyl hexylphosphonate 
• 111-25-1 1-bromo-hexane 
• 122-52-1 triethyl phosphite 
• 16165-66-5 diethyl hexylphosphonate 
• 592-41-6 1-hexene 
• 26584-01-0 C₁₅H₂₅N₂O₅PS 
• 26579-98-6 Dimethyl-1-diazohexan-phosphonat 
• 23897-48-5 Dimethyl-1-hexenylphosphonat 
• 110-54-3 hexane 
• 6172-92-5 Hexyl-phosphonsaeure-dimethylester 
• 928-64-3 hexylphosphonic acid dichloride 

Downstream Products

• 16165-66-5 diethyl hexylphosphonate 
• 592-41-6 1-hexene 
• 110-54-3 hexane 

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 polymerization kinetics of acrylamide phosphonic acids and esters as new dentine adhesives

In restorative dentistry, acrylamide monomers bearing phosphonic acid moieties have proved to be useful species for the formulation of dental self-etch adhesives since they provide enhanced adhesion to hydroxyapatite and are not subject to hydrolysis, thus potentially improving their adhesive durability. Previous studies have demonstrated that phosphonic acid acrylamides increase the rate of photopolymerization of diacrylamide monomers. To understand whether this rate acceleration is specific to the acrylamide function of the monomer, or due to the phosphonic acid group per se, or is applicable only with a crosslinking reaction, we have synthesized several acrylamide and methacrylate monomers bearing phosphonic acid or phosphonate moieties and studied their photopolymerization kinetics. The acrylamide phosphonic acid was found to accelerate the polymerization rate but similar monomers bearing a phosphonate ester group had a much smaller effect. A similar accelerating effect was observed when the phosphonic acid-based monomers were copolymerized with a monofunctional acrylamide monomer, excluding the possibility that the rate acceleration might be related to the crosslinking process. This rate effect is also observed when a nonpolymerizable organic phosphonic acid is present in the polymerizing medium. We suggest that the increase of the medium polarity is responsible for this rate enhancement effect.