4972-36-5

Basic information

• Product Name: diethyl piperidin-1-ylphosphonate
• Synonyms: Diethyl piperidin-1-ylphosphonate; phosphonic acid, P-1-piperidinyl-, diethyl ester
• CAS NO: 4972-36-5
• Molecular Formula: C₉H₂₀NO₃P
• Molecular Weight: 221.2338
• Mol File: 4972-36-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 272.2°C at 760 mmHg
• Flash Point: 118.4°C
• Density: 1.08g/cm³
• Vapor Pressure: 0.00616mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: diethyl piperidin-1-ylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl piperidin-1-ylphosphonate(4972-36-5)
• EPA Substance Registry System: diethyl piperidin-1-ylphosphonate(4972-36-5)

Safety Data

• Hazardous Substances Data: 4972-36-5(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 54436-53-2 O,O-diethyl (2,4-dinitrophenyl) phosphate triester 
• 311-45-5 paraoxon 
• 26773-65-9 N-piperidin-2-benzothiazole sulfenamide 
• 762-04-9 Diethyl phosphonate 

Downstream Products

• 6091-44-7 piperidine hydrochloride 
• 91411-14-2 [2-(2-Oxo-2-phenyl-ethyl)-piperidin-1-yl]-phosphonic acid diethyl ester 

Relevant articles and documents

Ionic liquids: Anion effect on the reaction of O,O-diethyl O-(2,4-dinitrophenyl) phosphate triester with piperidine

The reactions of O,O-diethyl 2,4-dinitrophenylphosphate triester (1) with piperidine in ionic liquids and four conventional organic solvents (COS) were subjected to kinetic and product studies. Analytical techniques (UV-vis and NMR) identified two pathways: nucleophilic attack at the phosphoryl center and at the C-1 aromatic carbon. The nucleophilic rate constants (kTN) for these parallel reactions were separated into two terms: kPN and kArN for the corresponding electrophilic centers. Both the rate and the selectivities of the reactions are strongly dependent on the nature of the ionic liquid used, and a good correlation with the solvent acceptor capacity to form hydrogen bonds (β) was observed. Remarkably, an exclusive attack at the phosphoryl center was found using [Bmim]DCA, [Bmpyrr]DCA and [Bmpy]DCA as the reaction solvents. In contrast, with [Bmim]PF6 as the reaction solvent, attack at the C-1 aromatic was the main path (94%). These results suggest that ionic liquids can be considered to be designer solvents because by an appropriate choice of the anion it is possible to steer the selectivity of this reaction. This journal is

Nucleophilic substitution reactions of diethyl 4-nitrophenyl phosphate triester: Kinetics and mechanism

The reactions of diethyl 4-nitrophenyl phosphate (1) with a series of nucleophiles: phenoxides, secondary alicyclic (SA) amines, and pyridines are subjected to a kinetic study. Under excess of nucleophile, all the reactions obey pseudo-first-order kinetics and are first order in the nucleophile. The nucleophilic rate constants (kN) obtained are pH independent for all the reactions studied. The Bronsted-type plot (log kN vs. pKa nucleophile) obtained for the phenolysis is linear with slope β=0.21; no break was found at pKa 7.5, consistent with a concerted mechanism. The Bronsted-type plots for the SA aminolysis and pyridinolysis are linear with slopes β=0.39 and 0.43, respectively, also suggesting concerted processes. The concerted mechanisms for the latter reactions are proposed on the basis of the lack of break in the Bronsted-type plots and the instability of the hypothetical pentacoordinate intermediates formed in these reactions.