65567-06-8

Basic information

• Product Name: LITHIUM DIPHENYLPHOSPHIDE
• Synonyms: LITHIUM DIPHENYLPHOSPHIDE;Lithium diphenylphosphide solution;LITHIUM DIPHENYLPHOSPHIDE, 0.5M SOLUTION;Lithium diphenylphosphide solution 0.5 in THF;Lithium diphenylphosphide, 0.5M solution in THF, AcroSeal;Diphenyl lithium phosphide;Diphenylphosphine lithium salt;Diphenylphosphino)lithium
• CAS NO: 65567-06-8
• Molecular Formula: C₁₂H₁₀LiP
• Molecular Weight: 192.12
• Product Categories: Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors
• Mol File: 65567-06-8.mol

Chemical Properties

• Boiling Point: 65-67 °C
• Flash Point: -20 °C
• Appearance: Orange to red/Liquid
• Density: 0.925 g/mL at 25 °C
• CAS DataBase Reference: LITHIUM DIPHENYLPHOSPHIDE(CAS DataBase Reference)
• NIST Chemistry Reference: LITHIUM DIPHENYLPHOSPHIDE(65567-06-8)
• EPA Substance Registry System: LITHIUM DIPHENYLPHOSPHIDE(65567-06-8)

Safety Data

• Hazard Codes: F,C,N
• Statements: 11-19-20/21/22-34-50/53-40-37
• Safety Statements: 16-26-27-36/37/39-45-61
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 2
• Hazardous Substances Data: 65567-06-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Lithium diphenylphosphide is used as a reducing agent for introducing the diphenylphosphide group into various organic compounds, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, lithium diphenylphosphide is utilized as a key reagent in the synthesis of active pharmaceutical ingredients, contributing to the development of new drugs and therapeutic agents.
Used in Fine Chemicals Production:
Lithium diphenylphosphide is employed as a reagent in the production of fine chemicals, where its ability to form carbon-carbon bonds and reduce ketones is essential for creating high-quality specialty chemicals for various applications.

InChI:InChI=1/C12H10P.Li/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;/q-1;+1/rC12H10LiP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 603-35-0 triphenylphosphine 
• 829-85-6 diphenylphosphane 
• 1663-45-2 1,2-bis-(diphenylphosphino)ethane 
• 109-72-8 n-butyllithium 
• 94901-37-8 {Ni(C₁₂H₁₀P)2(Diphenylphosphin)2} 
• 591-51-5 phenyllithium 
• 507-20-0 tertiary butyl chloride 
• 7439-93-2 lithium 
• 829-84-5 dicyclohexylphosphane 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 15475-27-1 potassium diphenylphosphine 
• 6372-40-3 isopropyldiphenylphosphine 
• 6002-34-2 tert-butyldiphenylphosphine 

Downstream Products

• 38202-37-8 (trans-2-hydroxycyclooctyl)diphenylphosphine oxide 
• 34218-69-4 cis,trans-1,4-Cyclooctadien 
• 13119-09-0 1,3-di(diphenylphosphino)-2-oxapropane 
• 40612-18-8 (E)-1,2-bis(diphenylphosphoryl)ethene 
• 13119-14-7 diphenylphosphino(methylthio)methane 
• 68899-50-3 (2-methoxyethyl)diphenylphosphine 
• 5055-12-9 (2-ethoxyethyl)(diphenyl)phosphine 
• 59386-70-8 3-Chlor-2,2-dimethylpropyldiphenylphosphin 
• 59386-56-0 3,3-dimethyl-1,1-diphenyl-phosphetanium; iodide 
• 69249-11-2 C₁₈H₁₀F₈P₂ 
• 69249-12-3 C₄₂H₃₀F₆P₄ 
• 70143-03-2 Z-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide 
• 13303-62-3 E-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide 
• 7608-17-5 2-diphenylphosphino-1-phenylethyne 

Relevant articles and documents

A Palladium-Free Sonogashira Coupling Protocol Employing an in Situ Prepared Copper/Chelating 1,2,3-Triazolylidene System

A new, palladium-free Sonogashira coupling reaction protocol using a catalytic system that comprises a simple, cheap, widely available copper salt and a chelating 1,2,3-triazolylidene ligand precursor is reported. This protocol provides the desired coupling products in moderate to very good yields.

Atypical and Asymmetric 1,3-P,N Ligands: Synthesis, Coordination and Catalytic Performance of Cycloiminophosphanes

Novel seven-membered cyclic imine-based 1,3-P,N ligands were obtained by capturing a Beckmann nitrilium ion intermediate generated in situ from cyclohexanone with benzotriazole, and then displacing it by a secondary phosphane under triflic acid promotion. These “cycloiminophosphanes” possess flexible non-isomerizable tetrahydroazepine rings with a high basicity; this sets them apart from previously reported iminophophanes. The donor strength of the ligands was investigated by using their P-κ1- and P,N-κ2-tungsten(0) carbonyl complexes, by determining the IR frequency of the trans-CO ligands. Complexes with [RhCp*Cl2]2 demonstrated the hemilability of the ligands, giving a dynamic equilibrium of κ1 and κ2 species; treatment with AgOTf gives full conversion to the κ2 complex. The potential for catalysis was shown in the RuII-catalyzed, solvent-free hydration of benzonitrile and the RuII- and IrI-catalyzed transfer hydrogenation of cyclohexanone in isopropanol. Finally, to enable access to asymmetric catalysts, chiral cycloiminophosphanes were prepared from l-menthone, as well as their P,N-κ2-RhIII and a P-κ1-RuII complexes.

Room-temperature reduction of sulfur hexafluoride with metal phosphides

Upon treatment with sulfur hexafluoride, alkali metal diphenyl or dicyclohexyl phosphides are oxidized within seconds to tetraphenyl or tetracyclohexyl diphosphines. When bulky di-tert-butylphosphide is employed, fluorophosphine intermediates are detected. This is the first reported reaction of sulfur hexafluoride with metal phosphides, and a rare example of reactivity of sulfur hexafluoride at ambient temperature. This journal is

Electrocatalytic property, anticancer activity, and density functional theory calculation of [NiCl(P^N^P)]Cl.EtOH

This study describes the electrocatalytic, anticancer, and density functional theory (DFT) studies of a nickel complex, [NiCl(P^N^P)]Cl.EtOH, based on a neutral P^N^P-type pincer ligand (P^N^P = bis[(2-diphenylphosphino)ethyl]amine). The ligand was synthesized without time-consuming and costly amine protection. It was characterized by 1H NMR, 31P NMR, Fourier transform infrared (FT-IR), UV–vis, and single-crystal X-ray diffraction. The complex was isolated as a solvated chloride salt and characterized by FT-IR, UV–visible, 1H NMR, 13C NMR, and 31P NMR spectroscopies as well as single-crystal X-ray diffraction and CHN analysis. The ligand and complex crystallized in a monoclinic P21/c space group. The molecular structure of the complex contains a four-coordinated distorted nickel ion with square-planar geometry. The electrocatalytic hydrogen ion reduction was studied for the nickel complex in an acidic non-aqueous medium. Cyclic voltammetry studies showed that this complex is an efficient electrocatalyst for hydrogen evolution at the potential of the Ni(II/I) couple. As a potential anticancer agent, the biological activities of the Ni complex were tested against two human cancer cell lines (MCF7 and HT29). The IC50 results demonstrated that the nickel complex has better cytotoxic activity than cis-platin against the human breast cancer cell (MCF7) line. DFT calculations were performed to study the kinetics and thermodynamics of the pincer ligand's synthetic procedure and its Ni complex. Time-dependent DFT calculations were performed to calculate the pincer ligand's UV–vis spectra and the complex, which was in agreement with the experimental data. To assign the calculated UV spectra, molecular orbital calculations were performed. Finally, a modified mechanism was proposed for the electrocatalytic hydrogen ion reduction by [Ni(P^N^P)Cl]Cl.EtOH. The theoretical calculations showed that the cycle is thermodynamically favorable.

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.

Synthesis, structural and toxicological investigations of quarternary phosphonium salts containing the P-bonded bioisosteric CH2F moiety

Tertiary alkyl, aryl or amino phosphines PR3 (R = Me, nBu, C2H4CN, NEt2) and the bis[(2-diphenylphosphino)phenyl]ether (POP) were allowed to react with fluoroiodomethane to produce fluoromethyl phosphonium salts in yields between 60-99%. The compounds were characterized by vibrational and NMR spectroscopy and in most cases also by single crystal X-ray diffraction. Diphenyl(fluoromethyl) phosphine was synthesized as a mixed aryl-alkyl-phosphine and the TEP value (Tolman electronic parameter) was determined in order to explain its low reactivity. The molecular and crystal structures of the new fluoromethyl phosphonium salts [R3PCH2F]I with R = Me, C2H2CN and NEt2 as well as of the salt resulting from the fluoromethylation of POP provided additional information on the structural behavior of the bioisoster CH2F group bonded to phosphorus. Hydrogen bonding in the crystal is compared with that observed in the crystal structure of PPh3CH2FI. The toxicity of the sufficiently water soluble salt [Me3PCH2F]I was investigated and the toxicological effect of the CH2F group was compared to that of the bioisoster CH2OH group in THPS. This journal is

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CATALYST COMPOSITION COMPRISING THE COMBINATION OF A MONOPHOPSPHINE, A TETRAPHOSPHINE LIGAND AND A HYDROFORMYLATION PROCESS USING IT

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