2240-47-3

Basic information

• Product Name: imidotriphenylphosphorus
• Synonyms: imidotriphenylphosphorus;Iminotriphenylphosphorane;N-(Triphenylphosphoranylidene)amine;Triphenylphosphine imide;Triphenylphosphinimine;Triphenylphosphine imine
• CAS NO: 2240-47-3
• Molecular Formula: C₁₈H₁₆NP
• Molecular Weight: 275.284221
• EINECS: 218-807-3
• Mol File: 2240-47-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 236 °C
• Boiling Point: 404.7°Cat760mmHg
• Flash Point: 198.6°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 2.16E-06mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: imidotriphenylphosphorus(CAS DataBase Reference)
• NIST Chemistry Reference: imidotriphenylphosphorus(2240-47-3)
• EPA Substance Registry System: imidotriphenylphosphorus(2240-47-3)

Safety Data

• Hazardous Substances Data: 2240-47-3(Hazardous Substances Data)

Usage

General Description

Imidotriphenylphosphorus is an organophosphorus compound with the chemical formula (C6H5)3P=NR. It is commonly used as a ligand in coordination chemistry and is known for its ability to form stable metal complexes. Imidotriphenylphosphorus is a strong electron donor, making it useful in catalytic applications and as a stabilizing agent for reactive metal compounds. It has been utilized in the synthesis of various organic compounds and is also employed in the production of pharmaceuticals and agrochemicals. Additionally, imidotriphenylphosphorus has been studied for its potential use in optical and electronic materials due to its unique electronic and structural properties.

InChI:InChI=1/C18H16NP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H

Upstream product

• 38011-30-2 bis(triphenyl-λ⁵-phosphanylidene)ammonium fluoride 
• 21050-13-5 bis(triphenylphosphine)iminium chloride 
• 603-35-0 triphenylphosphine 
• 15318-33-9 trans-carbonyl(chloro)bis(triphenylphosphine)rhodium(I) 
• 67-56-1 methanol 
• 791-28-6 Triphenylphosphine oxide 
• 916599-59-2 α-azidophenylacetonitrile 
• 15931-69-8 bromure de triphenyl aminophosphonium 
• 74255-76-8 (triphenylphosphoranylidene)ammonium azide 
• 15729-44-9 amino(triphenyl)phosphonium chloride 
• 13989-64-5 triphenylphosphine-N-tertbutylimine 

Downstream Products

• 852817-92-6 [PtCl₄(NH=C(Et)N=PPh₃)2] 
• 13916-35-3 lithium triphenylphosphonium azayldiide 
• 28049-42-5 C₁₈H₁₅Cl₇N₅P₅ 
• 16151-27-2 (Triphenylphosphazenyl)pentachlorocyclotriphosphazene 
• 24736-44-5 2-[5,5-dimethyl-3-(triphenyl-λ⁵-phosphanylideneamino)-cyclohex-2-enylidenemethyl]-3-ethyl-benzothiazolium; iodide 
• 24668-31-3 3-ethyl-2-thioxo-5-[7-(triphenyl-λ⁵-phosphanylideneamino)-4,4a,5,6-tetrahydro-3H-naphthalen-2-ylidene]-thiazolidin-4-one 
• 51944-78-6 C₄₂H₃₅ClN₄P₄ 
• 42564-07-8 C₂₅H₂₉ClN₂O₄P₂ 
• 213908-78-2 (Z)-ethyl 3,3,3-trifluoro-2-iminopropionate 
• 213908-78-2 (E)-ethyl 3,3,3-trifluoro-2-iminopropionate 
• 1599437-74-7 C₂₃H₂₁F₃NO₃P 

Relevant articles and documents

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Structure and Reactivity of a Manganese(VI) Nitrido Complex Bearing a Tetraamido Macrocyclic Ligand

Manganese complexes in +6 oxidation state are rare. Although a number of Mn(VI) nitrido complexes have been generated in solution via one-electron oxidation of the corresponding Mn(V) nitrido species, they are too unstable to isolate. Herein we report the isolation and the X-ray structure of a Mn(VI) nitrido complex, [MnVI(N)(TAML)]- (2), which was obtained by one-electron oxidation of [MnV(N)(TAML)]2- (1). 2 undergoes N atom transfer to PPh3 and styrenes to give Ph3P═NH and aziridines, respectively. A Hammett study for various p-substituted styrenes gives a V-shaped plot; this is rationalized by the ability of 2 to function as either an electrophile or a nucleophile. 2 also undergoes hydride transfer reactions with NADH analogues, such as 10-methyl-9,10-dihydroacridine (AcrH2) and 1-benzyl-1,4-dihydronicotinamide (BNAH). A kinetic isotope effect of 7.3 was obtained when kinetic studies were carried out with AcrH2 and AcrD2. The reaction of 2 with NADH analogues results in the formation of [MnV(N)(TAML-H+)]- (3), which was characterized by ESI/MS, IR spectroscopy, and X-ray crystallography. These results indicate that this reaction occurs via an initial "separated CPET"(separated concerted proton-electron transfer) mechanism; that is, there is a concerted transfer of 1 e- + 1 H+ from AcrH2 (or BNAH) to 2, in which the electron is transferred to the MnVI center, while the proton is transferred to a carbonyl oxygen of TAML rather than to the nitrido ligand.

Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene

A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of ?1.70 V vs. saturated calomel electrode (SCE) for the couple involving the neutral organic donor and its dication. This highly reducing organic compound can be isolated (44 %) or more conveniently generated in situ by a deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive S N bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.

The reaction of fullerene C60 with halogen azides

Reaction of fullerene C60 and halogen azides (IN3, BrN3) gives 1-halo-2-azidofullerenes, whose structures were proved by NMR and IR spectroscopy, MALDI-TOF mass spectrometry, and by their chemical transformations.