4441-17-2

Basic information

• Product Name: 1,1',1''-phosphinoylidynetripiperidine
• Synonyms: 1,1',1''-phosphinoylidynetripiperidine;TRIPIPERIDINOPHOSPHINEOXIDE;1,1'',1,''-PHOSPHINYLIDYNETRIPIPERIDINE;Tripiperidinophosphine oxide,98%;1-di(piperidin-1-yl)phosphorylpiperidine;1-dipiperidinophosphorylpiperidine
• CAS NO: 4441-17-2
• Molecular Formula: C₁₅H₃₀N₃OP
• Molecular Weight: 283.392561
• EINECS: 224-663-2
• Mol File: 4441-17-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 75.5°C
• Boiling Point: 434°Cat760mmHg
• Flash Point: 216.3°C
• Appearance: /solid
• Density: 1.13g/cm³
• CAS DataBase Reference: 1,1',1''-phosphinoylidynetripiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1',1''-phosphinoylidynetripiperidine(4441-17-2)
• EPA Substance Registry System: 1,1',1''-phosphinoylidynetripiperidine(4441-17-2)

Safety Data

• Hazardous Substances Data: 4441-17-2(Hazardous Substances Data)

Usage

Phosphorus-containing compound

Contains a phosphinoyl group
The presence of a phosphinoyl group (P=O) is a key feature of this compound, which contributes to its unique chemical properties and potential applications.

Structure

Three piperidine rings and a phosphinoyl group attached to the nitrogen atoms
The compound's structure consists of three piperidine rings (a type of heterocyclic compound with a nitrogen atom in the ring) connected through a phosphinoyl group.

Application

Used as a ligand in coordination chemistry
As a ligand, 1,1',1''-phosphinoylidynetripiperidine can form complexes with metal ions, which can be used to study the properties and reactivity of these metal complexes.

Potential applications

Investigated for use in catalysis
The compound's unique structure and properties make it a candidate for use in catalytic processes, which are essential for various chemical reactions and industrial applications.

Chiral ligand

Studied for potential use in asymmetric catalysis
As a chiral ligand, 1,1',1''-phosphinoylidynetripiperidine can be used to induce chirality in the products of catalytic reactions, which is important for the synthesis of enantiomerically pure compounds.

Development

Potential use in the development of new and efficient catalytic processes
The compound's unique properties and potential applications make it a promising candidate for the development of new catalytic processes, which could lead to more efficient and environmentally friendly chemical production methods.

Upstream product

• 110-89-4 piperidine 
• 10025-87-3 trichlorophosphate 

Relevant articles and documents

A new six-coordinate organotin(IV) complex of OP[NC5H10]3: A comparison with an analogous five-coordinate complex by means of X-ray crystallography, Hirshfeld surface analysis and DFT calculations

A new six-coordinate organotin(IV)-phosphoric triamide complex of OP[NC5H10]3?=?OP was synthesized ([Cl2Sn(CH3)2(OP)2], 1) and characterized by X-ray crystallography and spectroscopic methods (FT-IR, UV–Vis, and 1H/13C/31P-NMR). The crystal structures of 1 and the analogous previously reported five-coordinate complex [Cl2Sn(CH3)2(OP)] (IZOVIE) were compared on a structural level and by computational means using Hirshfeld surface analysis, density functional theory calculations and the atom in molecule method. The investigation of intermolecular interactions in the crystal structures of the two complexes by the Hirshfeld surface method indicates that in the absence of normal hydrogen bonds, the chlorine-based interactions H?Cl/Cl?H (for 1 and IZOVIE) and Cl?Sn/Sn?Cl (for IZOVIE) play a determinant role in the molecular assemblies. However, the prominent contacts are of H?H type. From calculated electronic parameters such as bond order, Mulliken charge and electron delocalization energy, it was found that the Sn-OP contact has a lower strength in IZOVIE than in 1, suggesting more ionic character of the metal-oxygen contact in five-coordinate complex IZOVIE. Furthermore, we discuss the similarities and differences of the two complexes 1 and IZOVIE derived from the same ligand OP by density functional theory calculations to present an insight into the organotin(IV)-phosphoric triamide coordination chemistry affected by different geometries and coordination numbers.

Rapid Analysis of Tetrakis(dialkylamino)phosphonium Stability in Alkaline Media

Hydroxide-stable organic cations are crucial components for ion-transport processes in electrochemical energy systems, and the tetrakis(dialkylamino)phosphonium cation is a promising candidate for this application. These phosphoniums are known to be highly resistant to alkaline media; however, very few investigations have systematically evaluated how these cations decompose in the presence of hydroxide or alkoxide anions. The excellent stability of several tetraaminophosphoniums in 2 M KOH/CH3OH at 80 °C led us to design experiments for the rapid assessment of phosphonium degradation in homogeneous solution and under phase-transfer conditions. The analysis illustrated how substituents around the cation core affect both degradation pathways and rates. β-H elimination and direct attack at the phosphorus atom are the most common degradation pathways observed in an alcoholic solvent, while α-H abstraction and direct attack are observed under phase-transfer conditions (PhCl and 50 wt % NaOH/H2O). The collected data provided a relative stability comparison for this family of cations to enable future design improvements and illustrated the utility of using multiple tests for degradation studies.

Phosphoramide additives for preparation of organic carbonates

An organic carbonate such as dimethyl carbonate is prepared by reacting an alcohol such as methanol with carbon monoxide oxygen in the presence of a catalyst system containing Cu(OMe)Cl as a catalyst and a phosphoramide as an additive for the catalyst system.