5137-70-2

Basic information

• Product Name: N-DODECYLPHOSPHONIC ACID
• Synonyms: 1-dodecanephosphonicacid;dodecylphosphonicacid;n-dodecanephosphonicacid;DDPA;LABOTEST-BB LT00408923;N-DODECYLPHOSPHONIC ACID;n-Dodecylphosphonicacid,min.97%;1-Dodecylphosphonic acid, 95%
• CAS NO: 5137-70-2
• Molecular Formula: C₁₂H₂₇O₃P
• Molecular Weight: 250.31
• EINECS: 225-897-8
• Product Categories: organic phosphonic acid
• Mol File: 5137-70-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 283°C (estimate)
• Flash Point: 185.9 °C
• Appearance: white to off-white/Powder
• Density: 0.9360 (estimate)
• Vapor Pressure: 5.9E-07mmHg at 25°C
• Refractive Index: 1.462
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Sparingly soluble in water.
• CAS DataBase Reference: N-DODECYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-DODECYLPHOSPHONIC ACID(5137-70-2)
• EPA Substance Registry System: N-DODECYLPHOSPHONIC ACID(5137-70-2)

Safety Data

• RIDADR: UN3261
• WGK Germany: 3
• RTECS: SZ7875000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5137-70-2(Hazardous Substances Data)

Usage

Description

N-DODECYLPHOSPHONIC ACID is an organic compound with the chemical structure RP(O)(OH)2, which features both non-polar organic hydrophobic groups and anionic inorganic hydrophilic groups. This bifunctional structure endows it with surfactant properties, making it a versatile compound in various applications.

Uses

Used in Surfactant Applications:
N-DODECYLPHOSPHONIC ACID is used as a surfactant for its ability to lower surface tension between two liquids or a liquid and a solid, enhancing the interaction between different substances.
Used in Detergent Industry:
N-DODECYLPHOSPHONIC ACID is used as a detergent due to its effectiveness in removing dirt and stains, as well as its ability to disperse oils and grease.
Used in Dispersant Applications:
In the field of dispersants, N-DODECYLPHOSPHONIC ACID is used to prevent the aggregation of particles, ensuring a uniform distribution of substances in a solution.
Used in Emulsifier Applications:
N-DODECYLPHOSPHONIC ACID is used as an emulsifier to stabilize mixtures of two immiscible liquids, such as oil and water, by reducing the interfacial tension between them.
Used in Chelating Agent Applications:
As a chelating agent, N-DODECYLPHOSPHONIC ACID is used to bind and sequester metal ions, preventing them from participating in unwanted reactions.
Used in Surface Energy Tuning:
N-DODECYLPHOSPHONIC ACID is used for tuning the surface energy, wetting, and work function of metal oxides, which can be crucial in various industrial processes and applications.
Used in Photonics and Optoelectronics:
Although not explicitly mentioned in the provided materials, due to its surfactant properties and potential for interaction with light, N-DODECYLPHOSPHONIC ACID could potentially be used in photonics and optoelectronics for applications such as waveguides, optical sensors, or nonlinear optical components.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H27O3P/c1-2-3-4-5-6-7-8-9-10-11-12-16(13,14)15/h2-12H2,1H3,(H2,13,14,15)

Synthetic route

dodecylphosphonate de dimethyle (16693-57-5) → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
With trimethylsilyl bromide In dichloromethane at 40℃; for 3h;	90%

1-dodecylbromide (143-15-7) → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
Stage #1: 1-dodecylbromide 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: hexane 2: concentrated aqueous HCl View Scheme
Stage #1: 1-dodecylbromide With triethyl phosphite In water at 160 - 190℃; for 4h; Stage #2: With hydrogen bromide In water for 3h; Reflux;

dodecyl-phosphonic acid dibutyl ester (5929-68-0) → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
With hydrogenchloride
With hydrogen bromide

C18H43O3PSi2 → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
With methanol In dichloromethane for 1h;
With water In acetone at 20℃; for 1h;
With methanol for 0.166667h;

1-dodecene (112-41-4) + 2,3-didecyl-1,3-butadiene2-decyl-1,3-tetradecadiene → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / di-tert-butyl peroxide / 10 h / 135 °C 2: 90 percent / BrSiMe3 / CH2Cl2 / 3 h / 40 °C View Scheme

diethyl n-dodecylphosphonate (4844-38-6) → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 1.5 h / 0 - 20 °C 2: H2O / acetone / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 20 °C 2: MeOH / CH2Cl2 / 1 h View Scheme

1-dodecene (112-41-4) + O2 → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / (tBuO)2 / 15 h / 135 °C 2: CH2Cl2 / 2 h / 20 °C 3: MeOH / CH2Cl2 / 1 h View Scheme

1-dodecylbromide (143-15-7) + copper (I)-benzenethiolate → dodecylphosphonic acid (5137-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 2: aq. HBr View Scheme

K8[γ-SiW10O36]*12H2O + dodecylphosphonic acid (5137-70-2) + tetramethylammonium bromide (64-20-0) → γ-(tetramethylammonium)3K[SiW10O36(OPC12H25)2]

Conditions	Yield
With hydrogenchloride In acetonitrile Reflux;	70%

dodecylphosphonic acid (5137-70-2) + α-Na10[SiW9O34] + tetramethylammonium bromide (64-20-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (tetramethylammonium)2,5Na3,5[SiW9O34(OPC12H25)2] dimethylformamide solvate

Conditions	Yield
With hydrogenchloride at 100℃;	70%

dodecylphosphonic acid (5137-70-2) + α-Na10[SiW9O34] + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Na6[SiW9O34(OPC12H25)2] dimethylformamide solvate

Conditions	Yield
With hydrogenchloride at 100℃;	55%

dodecylphosphonic acid (5137-70-2) → n-dodecylphosphonic acid dichloride (3586-98-9)

Conditions	Yield
With phosphorus pentachloride

dodecylphosphonic acid (5137-70-2) + cytidine 5'-monophosphomorpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt (76742-18-2) → C21H39N3O10P2

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

dodecylphosphonic acid (5137-70-2) + Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester morpholin-4-yl ester → C21H39N3O9P2

Conditions	Yield
With pyridine In toluene for 74h; Ambient temperature;

dodecylphosphonic acid (5137-70-2) + Phosphoric acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester morpholin-4-yl ester → C22H40N2O10P2

Conditions	Yield
With pyridine In toluene for 74h; Ambient temperature;

dodecylphosphonic acid (5137-70-2) + Phosphoric acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester morpholin-4-yl ester → C22H39N5O9P2

Conditions	Yield
With pyridine In toluene for 74h; Ambient temperature;

dodecylphosphonic acid (5137-70-2) → 1-dodecyldifluorophosphonate (682343-00-6)

Conditions	Yield
With dimethylaminosulphur trifluoride In chloroform at 0 - 20℃; for 0.333333h;

dodecylphosphonic acid (5137-70-2) → Isopropyldodecylfluorophosphonate

Conditions	Yield
Multi-step reaction with 2 steps 1: (CH3)2NSF3 / CHCl3 / 0.33 h / 0 - 20 °C 2: Et3N / diethyl ether / 1 h / 0 °C View Scheme

dodecylphosphonic acid (5137-70-2) → dodecylphosphonate de dimethyle (16693-57-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5 2: Py View Scheme

zirconyl chloride octahydrate + dodecylphosphonic acid (5137-70-2) + phosphonomethanesulfonic acid (73300-71-7) → Zr(4+)*(O3PCH2SO3H)(2-)*O3PC12H25(2-)=Zr{(O3PCH2SO3H)0.5(O3PC12H25)0.5}2 (145425-42-9)

Conditions	Yield
In water

zirconyl chloride octahydrate + dodecylphosphonic acid (5137-70-2) + phosphonomethanesulfonic acid (73300-71-7) → Zr(4+)*0.8O3PCH2SO3H(2-)*1.2O3PC12H25(2-)=Zr[(O3PCH2SO3H)0.4(O3PC12H25)0.6]2

Conditions	Yield
In water

zirconyl chloride octahydrate + dodecylphosphonic acid (5137-70-2) + phosphonomethanesulfonic acid (73300-71-7) → Zr(4+)*1.2O3PCH2SO3H(2-)*0.8O3PC12H25(2-)=Zr[(O3PCH2SO3H)0.6(O3PC12H25)0.4]2

Conditions	Yield
In water

zirconyl chloride octahydrate + dodecylphosphonic acid (5137-70-2) → zirconium dodecyl phosphonate

Conditions	Yield
In water

dodecylphosphonic acid (5137-70-2) → 2C12H26O3P(1-)*Ca(2+)

Conditions	Yield
With calcium(II) nitrate tetrahydrate; sodium hydroxide In tetrahydrofuran; water at 20℃; for 96h;

Upstream product

• 5929-68-0 dodecyl-phosphonic acid dibutyl ester 
• 16693-57-5 dodecylphosphonate de dimethyle 
• 112-41-4 1-dodecene 
• 4844-38-6 diethyl n-dodecylphosphonate 
• 143-15-7 1-dodecylbromide 

Downstream Products

• 615250-02-7 Isopropyldodecylfluorophosphonate 
• 4844-38-6 diethyl n-dodecylphosphonate 

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.

Microwave michaelis-becker synthesis of diethyl phosphonates, tetraethyl diphosphonates, and their total or partial dealkylation

Diethyl phosphonates and tetraethyl alkyldiphosphonates were efficiently and rapidly prepared via the Michaelis-Becker reaction, under microwave irradiation. These compounds were then hydrolyzed to phosphonic and diphosphonic acids or selectively monodealkylated to give monoesters of phosphonic acids and symmetrical diethyl esters of diphosphonic acids. These reactions were also achieved rapidly in satisfactory yields with microwave methodology. This methodology was applied with success to the functionalization of a polymer resin.

Cannabinoid CB1 receptor chemical affinity probes: Methods suitable for preparation of isopropyl [11,12-3H]dodecylfluorophosphonate and [11,12-3H]dodecanesulfonyl fluoride

Preparations of isopropyl dodec-11-enylfluorophosphonate and dodec-11-enesulfonyl fluoride are described along with conditions for their reduction with hydrogen (or potentially tritium) gas to the 1-dodecane derivatives as candidate high-potency (IC50 0.5-7 nM) chemical affinity probes for the mouse brain cannabinoid CB1 receptor and fatty acid amide hydrolase.