6874-60-8

Basic information

• Product Name: 1-DECYLPHOSPHONIC ACID
• Synonyms: 1-decanephosphonicacid;decyl-phosphonicaci;1-DECYLPHOSPHONIC ACID;LABOTEST-BB LT00408922;DPA;N-DECYLPHOSPHONIC ACID;SALOR-INT L496200-1EA;decylphosphonic acid
• CAS NO: 6874-60-8
• Molecular Formula: C₁₀H₂₃O₃P
• Molecular Weight: 222.26
• EINECS: 229-975-2
• Product Categories: organic phosphonic acid
• Mol File: 6874-60-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 100-101°C
• Boiling Point: 355.8 °C at 760 mmHg
• Flash Point: 169 °C
• Appearance: white to off-white/Powder
• Density: 1.044
• Vapor Pressure: 5.07E-06mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: 2-8°C
• BRN: 1771572
• CAS DataBase Reference: 1-DECYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DECYLPHOSPHONIC ACID(6874-60-8)
• EPA Substance Registry System: 1-DECYLPHOSPHONIC ACID(6874-60-8)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34-14
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• WGK Germany: 3
• RTECS: SZ7525000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6874-60-8(Hazardous Substances Data)

Usage

Uses

1-Decylphosphonic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It is used in stabilizing dye-sensitized solar cell.

General Description

Decylphosphonic acid(DPA) is a phosphono-alkane derivative that forms a self-assembled monolayer(SAM) that can be used as an interfacial modifier.

InChI:InChI=1/C10H23O3P/c1-2-3-4-5-6-7-8-9-10-14(11,12)13/h2-10H2,1H3,(H2,11,12,13)

Synthetic route

diethyl 1-decylphosphonate (16165-68-7) → 1-decylphosphonic acid (6874-60-8)

Conditions	Yield
With water at 400℃; under 232523 Torr; for 0.0333333h; Supercritical conditions; Autoclave;	98%
Stage #1: diethyl n-decylphosphonate With boron tribromide In hexane; toluene at 70℃; for 6h; Stage #2: With methanol In hexane; toluene at 20℃;	82%
With hydrogenchloride Heating;

1-bromo dodecane (112-29-8) → 1-decylphosphonic acid (6874-60-8)

Conditions	Yield
Stage #1: 1-bromo dodecane 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;	65%
Multi-step reaction with 2 steps 2: 6 N HCl / Heating View Scheme
Multi-step reaction with 2 steps 1: hexane 2: concentrated aqueous HCl View Scheme

n-decylphosphonous acid (4741-18-8) + hypophosphorous acid (14332-09-3) → 1-decylphosphonic acid (6874-60-8)

Conditions	Yield
With sodium hydroxide; potassium permanganate; sodium hydrogensulfite In water; acetone	49%

decyl-phosphonic acid dibutyl ester (36378-71-9) → 1-decylphosphonic acid (6874-60-8)

Conditions	Yield
With hydrogenchloride

1-Decene (872-05-9) → 1-decylphosphonic acid (6874-60-8)

Conditions	Yield
With phosphonic Acid; dibenzoyl peroxide

1-decylphosphonic acid (6874-60-8) + α-Na10[SiW9O34] + tetramethylammonium bromide (64-20-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (tetramethylammonium)2,5Na3,5[SiW9O34(OPC10H21)2] dimethylformamide solvate

Conditions	Yield
With hydrogenchloride at 100℃;	78%

K8[γ-SiW10O36]*12H2O + 1-decylphosphonic acid (6874-60-8) + tetramethylammonium bromide (64-20-0) → γ-(tetramethylammonium)3K[SiW10O36(OPC10H21)2]

Conditions	Yield
With hydrogenchloride In acetonitrile Reflux;	66%

1-decylphosphonic acid (6874-60-8) + α-Na10[SiW9O34] + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Na6[SiW9O34(OPC10H21)2] dimethylformamide solvate

Conditions	Yield
With hydrogenchloride at 100℃;	30%

1-decylphosphonic acid (6874-60-8) → n-decylphosphonic acid dichloride (14576-66-0)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;

1-decylphosphonic acid (6874-60-8) → ammonium 1-decylphosphonate (1353567-51-7)

Conditions	Yield
With ammonia In water

1-decylphosphonic acid (6874-60-8) → GENERIC INORGANIC CATION; decane-1-phosphonate

Conditions	Yield
With calcium chloride In water

1-decylphosphonic acid (6874-60-8) + ethylenediamine (107-15-3) → ethylenediaminium 1-decylphosphonate (1353567-52-8)

Conditions	Yield
In water

1-decylphosphonic acid (6874-60-8) + water (7732-18-5) + copper diacetate (142-71-2) → Cu(2+)*CH3(CH2)9PO3(2-)*H2O=Cu(CH3(CH2)9PO3)*H2O

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.;

1-decylphosphonic acid (6874-60-8) + copper diacetate (142-71-2) → Cu(2+)*CH3(CH2)9PO3(2-)=Cu(CH3(CH2)9PO3)

Conditions	Yield
In water High Pressure; acid mixed with aq. soln. of CuCl2 (3.5:3.7 molar ratio), sealed, heatedat 160°C for 24 h; cooled to room temp. in 24 h, filtered off, washed (H2O, EtOH), dried atroom temp.;

zirconyl propionate + 1-decylphosphonic acid (6874-60-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.66(hexylphosphonate)0.34*(x)H2O

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

zirconyl propionate + 1-decylphosphonic acid (6874-60-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.52(hexylphosphonate)0.48*(x)H2O

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

zirconyl propionate + 1-decylphosphonic acid (6874-60-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)1.04(hexylphosphonate)0.96*(x)H2O

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

zirconyl propionate + 1-decylphosphonic acid (6874-60-8) + phosphoric acid (86119-84-8, 7664-38-2) → Zr(O3POH)0.99(hexylphosphonate)1.01*(x)H2O

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

Upstream product

• 4741-18-8 n-decylphosphonous acid 
• 14332-09-3 hypophosphorous acid 
• 112-29-8 1-bromo dodecane 
• 16165-68-7 diethyl n-decylphosphonate 
• 872-05-9 1-Decene 
• 36378-71-9 decyl-phosphonic acid dibutyl ester 

Downstream Products

• 14576-66-0 n-decylphosphonic acid dichloride 

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.

Supercritical hydrothermal synthesis of carboxylic acid-surface- functionalized TiO2 nanocrystals: PH sensitive dispersion and hybridization with organic compounds

Surface-functionalized TiO2 (anatase) nanocrystals (NCs) (avg. d=6.7±1.6nm) were synthesized by a supercritical hydrothermal method. A phosphonic acid derivative was used as surface modifier of TiO2 NCs. It was verified that the phosphonic acids were bound to the surface of TiO 2 with very strong binding energy. The TiO2 NCs also exhibited extraordinarily high chemical stability. Such a strong binding between the phosphonic acid modifier and TiO2 had not been obtained by any other methods. The TiO2 NC showed sharp pH sensitive dispersion. Because of the functional as well as stable surface modifier layer, further manipulations on the surface using chemical reagents could be possible.

Phosphorus containing compounds as antihypercholesterolemic and antiatherosclerotic agents

Novel phosphorus containing compounds are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful in preventing the intestinal absorption of cholesterol and thus are useful in the treatment of hypercholesterolemia and atherosclerosis.