4671-75-4

Usage

Uses

Used in Nanoparticle Functionalization:
N-TETRADECYLPHOSPHONIC ACID is used as a functionalizing agent for nanoparticles to enhance their properties and performance in various applications.
Used in BaTiO3 Nanoparticle Surface Functionalization:
N-TETRADECYLPHOSPHONIC ACID is used as a surface functionalizer for BaTiO3 nanoparticles to improve their properties and performance in applications such as electronic devices and sensors.
Used in Copper Nanoparticle Protection:
N-TETRADECYLPHOSPHONIC ACID is used as a capping agent for copper nanoparticles to protect them from oxidation, enhancing their stability and performance in various applications.
Used in Quantum Dot Synthesis:
N-TETRADECYLPHOSPHONIC ACID is used as a capping agent in the synthesis of cadmium sulfate (CdS) core, which can be used in the fabrication of cadmium selenium (CdSe)/CdS core quantum dots (QDs). These QDs have potential applications in solar cells, LEDs, and other optoelectronic devices.
Used in White Light Emitting Diodes (wLED) Development:
N-TETRADECYLPHOSPHONIC ACID is used as a coating material on caesium lead bromide (CsPbBr3) perovskite quantum dots for the development of white light emitting diodes (wLED), which have potential applications in energy-efficient lighting and display technologies.

Physical state

N-TETRADECYLPHOSPHONIC ACID is a white to off-white powder.

Shipping Condition

Room Temperature; may vary elsewhere.

Biological Activity

tetradecyl phosphonate is a pan-antagonist of lysophosphatidic acid 1 (lpa1), lpa2, and lpa3 receptors. the ic50 value for inhibition of lpa-induced calcium mobilization was 10 μm, 5.5 μm, and 3.1 μm, respectively. at a concentration of 10 μm, tetradecyl phosphonate activates a peroxisome proliferator-activated receptor γ reporter construct 4-fold when compared with the controls and partially inhibits autotaxin with an ic50 value of approximately 3 μm [1].lysophosphatidic acid (lpa), also known as autotaxin (atx), is a lipid signalling molecule formed by the hydrolysis of lysophosphatidyl choline by lysophospholipase d [2]. lpa signals through four different g protein-coupled receptors, named as lpa1/edg-2, lpa2/edg-4, lpa3/edg-7, and lpa4/gpr23 [3]. it has been reported that lpa was involved in activating peroxisome proliferator-activated receptor γ (pparγ) [4].

references

[1]. durgam g g, virag t, walker m d, et al. synthesis, structure activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of pparγ, and inhibitors of autotaxin[j]. journal of medicinal chemistry, 2005, 48(15): 4919-4930.[2]. tokumura a, majima e, kariya y, et al. identification of human plasma lysophospholipase d, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase[j]. journal of biological chemistry, 2002, 277(42): 39436-39442.[3]. noguchi k, ishii s, shimizu t. identification of p2y9/gpr23 as a novel g protein-coupled receptor for lysophosphatidic acid, structurally distant from the edg family[j]. journal of biological chemistry, 2003, 278(28): 25600-25606.[4]. mcintyre t m, pontsler a v, silva a r, et al. identification of an intracellular receptor for lysophosphatidic acid (lpa): lpa is a transcellular pparγ agonist[j]. proceedings of the national academy of sciences, 2003, 100(1): 131-136.

InChI:InChI=1/C14H31O3P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18(15,16)17/h2-14H2,1H3,(H2,15,16,17)

Synthetic route

1-Bromotetradecane (112-71-0) → n-tetradecylphosphonic acid (4671-75-4)

Conditions	Yield
Stage #1: 1-Bromotetradecane 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;	50%
Multi-step reaction with 2 steps 1: hexane 2: concentrated aqueous HCl View Scheme

tetradecyl-phosphonic acid dibutyl ester (33512-29-7) → n-tetradecylphosphonic acid (4671-75-4)

Conditions	Yield
With hydrogenchloride

oxirane (75-21-8) + n-tetradecylphosphonic acid (4671-75-4) → O-β-Hydroxyaethyl-1-n-tetradecylphosphonat (59259-21-1)

Conditions	Yield
In benzene

n-tetradecylphosphonic acid (4671-75-4) + cytidine 5'-monophosphomorpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt (76742-18-2) → C23H43N3O10P2

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

n-tetradecylphosphonic acid (4671-75-4) + dihydrogen peroxide (7722-84-1) + benzene (71-43-2) + MoO3 → compound C28H60MoO10P2

n-tetradecylphosphonic acid (4671-75-4) + dihydrogen peroxide (7722-84-1) + benzene (71-43-2) + MoO3 → compound C28H60MoO8P2

Conditions	Yield
at 130℃;

n-tetradecylphosphonic acid (4671-75-4) → O-Methyl-O-β-hydroxyaethyl-tetradecylphosphonat (59259-19-7)

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

n-tetradecylphosphonic acid (4671-75-4) → Di-O-β-hydroxyaethyl-n-tetradecyl-1-phosphonat (40520-22-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene 3: benzene View Scheme

n-tetradecylphosphonic acid (4671-75-4) + cobalt acetylacetonate → cobalt(III) phosphide

Conditions	Yield
In further solvent(s) mixt. hexadecylamine and trioctylphosphine was heated at 140°C under vac. for 1 h, Co(acac)2 and tetradecylphosphonic acid were added at 100°C, stirred under N2, slowly heated to 340°C over 1 h, mixt. was kept at this temp. for 3 h; mixt. was cooled to 60°C, excess EtOH was added. ppt. was separeted by centrifugation, dried under vac.;

n-tetradecylphosphonic acid (4671-75-4) + copper diacetate (142-71-2) → Cu(2+)*CH3(CH2)13PO3(2-)=Cu(CH3(CH2)13PO3)

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.;

manganese oleate complex + n-tetradecylphosphonic acid (4671-75-4) → manganese(II) phosphate

Conditions	Yield
at 320℃; Inert atmosphere;

n-tetradecylphosphonic acid (4671-75-4) + iron(III) oleate (1120-45-2, 15114-26-8, 15114-27-9, 15114-31-5, 15114-32-6, 23335-74-2) → iron(III) phosphate (765207-04-3)

Conditions	Yield
at 320℃; for 1h; Inert atmosphere; High pressure;

n-tetradecylphosphonic acid (4671-75-4) + cobalt(II) oleate (1120-43-0, 4751-12-6, 14666-94-5, 15114-23-5, 15114-28-0, 19192-71-3) → cobalt phosphate

Conditions	Yield
at 320℃; Inert atmosphere;

n-tetradecylphosphonic acid (4671-75-4) + cadmium(II) acetate (543-90-8) → cadmium tetradecylphosphonic acid

Conditions	Yield
With octadec-1-ene; TOP at 300℃; Inert atmosphere; Schlenk technique;

Upstream product

• 33512-29-7 tetradecyl-phosphonic acid dibutyl ester 
• 112-71-0 1-Bromotetradecane 

Downstream Products

• 40520-22-7 Di-O-β-hydroxyaethyl-n-tetradecyl-1-phosphonat 
• 12134-02-0 cobalt(III) phosphide 

Relevant academic research and scientific papers

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.