5815-61-2

Usage

Uses

Used in Organometallic Chemistry:
TRIS(4-MORPHOLINO)PHOSPHINE is used as a ligand for its ability to coordinate with transition metals, facilitating various chemical reactions and contributing to the advancement of organometallic chemistry.
Used in Catalysis:
In the field of catalysis, TRIS(4-MORPHOLINO)PHOSPHINE is employed as a ligand to enhance the efficiency and selectivity of catalytic processes, leveraging its strong electron-donating properties.
Used in Pharmaceutical Industry:
TRIS(4-MORPHOLINO)PHOSPHINE is used as a key building block in the development and synthesis of pharmaceutical compounds, playing a crucial role in the creation of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, TRIS(4-MORPHOLINO)PHOSPHINE is utilized as a fundamental component in the production of various agrochemicals, including pesticides and fertilizers, to improve agricultural productivity and crop protection.

InChI:InChI=1/C22H25ClF3N5O2/c1-4-30(5-2)12-6-11-27-21(32)19-18(23)20-28-16(14-7-9-15(33-3)10-8-14)13-17(22(24,25)26)31(20)29-19/h7-10,13H,4-6,11-12H2,1-3H3,(H,27,32)

Upstream product

• 110-91-8 morpholine 
• 2283-11-6 hexaethylphosphoric triamide 
• 13368-42-8 4-(trimethylsilyl)morpholine 
• 685-83-6 bis(diethylamino)chlorophosphine 
• 22630-09-7 trimorpholylmethane 
• 75302-66-8 dimorpholinophosphinous chloride 
• 93374-14-2 phenyl dimorpholinophosphinite 
• 7719-12-2 phosphorus trichloride 

Downstream Products

• 22883-68-7 Benzyl-trimorpholinophosphoniumbromid 
• 6774-93-2 (4-hydroxy-phenyldiazenyl)-tri-morpholin-4-yl-phosphonium betaine 
• 3028-57-7 (2-hydroxy-3,5-dimethyl-phenyldiazenyl)-tri-morpholin-4-yl-phosphonium betaine 
• 14129-98-7 Trismorpholinophosphorothioat 
• 35045-30-8 (tri-morpholin-4-yl-λ⁵-phosphanylidene)-carbamic acid phenyl ester 
• 35045-27-3 4,4',4''-(N-benzoyl-phosphorimidoyl)-tris-morpholine 
• 94262-15-4 P,P,P-trimorpholino-N-phenylphosphazide 
• 114360-61-1 C₄₃H₅₂N₇O₉P 
• 114360-60-0 C₄₆H₅₀N₇O₈P 

Relevant academic research and scientific papers

Disentangling ligand effects on metathesis catalyst activity: Experimental and computational studies of ruthenium-aminophosphine complexes

Second-generation ruthenium olefin metathesis catalysts bearing aminophosphine ligands were investigated with systematic variation of the ligand structure. The rates of phosphine dissociation (k1; initiation rate) and relative phosphine reassociation (k-1) were determined for two series of catalysts bearing cyclohexyl(morpholino)phosphine and cyclohexyl(piperidino)phosphine ligands. In both cases, incorporating P-N bonds into the architecture of the dissociating phosphine accelerates catalyst initiation relative to the parent [Ru]-PCy3 complex; however, this effect is muted for the tris(amino)phosphine-ligated complexes, which exhibit higher ligand binding constants in comparison to those with phosphines containing one or two cyclohexyl substituents. These results, along with X-ray crystallographic data and DFT calculations, were used to understand the influence of ligand structure on catalyst activity. Especially noteworthy is the application of phosphines containing incongruent substituents (PR1R′2); detailed analyses of factors affecting ligand dissociation, including steric effects, inductive effects, and ligand conformation, are presented. Computational studies of the reaction coordinate for ligand dissociation reveal that ligand conformational changes contribute to the rapid dissociation for the fastest-initiating catalyst of these series, which bears a cyclohexyl-bis(morpholino)phosphine ligand. Furthermore, the effect of amine incorporation was examined in the context of ring-opening metathesis polymerization, and reaction rates were found to correlate well with catalyst initiation rates. The combined experimental and computational studies presented in this report reveal important considerations for designing efficient ruthenium olefin metathesis catalysts.

Studies on iodination reactions of phosphiniminocyclotrithiazenes

Iodination reactions of various phosphiniminocyclotrithiazenes [R 3PNS3N3; R = (i) phenyl-, (ii) morpholino-, and (iii) p-chlorophenyl-] have been studied under different experimental conditions. Iodination of Ph3PNS3N3 yields interesting products such as [(Ph3PN)2S3N 3]I3, ((Ph3PN)3S)2I 4, (Ph3PNH2)I3, ((Ph 3PSI2)2I2, and [(Ph 3PN)3SO]2I6 depending on the experimental conditions. All the products have been isolated and characterized by the spectroscopic and analytical techniques. Copyright Taylor & Francis Group, LLC.

Synthesis of N6,N6-dialkyladenine nucleosides using hexaalkylphosphorus triamides produced in situ

Reactions between secondary amines and phosphorus trichloride (PCl 3) leads to the formation of the corresponding tris(dialkylamino) phosphanes or hexaalkylphosphorus triamides [HAPTs: (R2N) 3P]. Treatment of silyl-protected 2′-deoxyinosine and acetyl-protected inosine with the HAPTs produced in situ, together with iodine (I2), leads to the formation of N6,N6- dialkyladenosine and -2′-deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I2 has been studied by 31P{1H} NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Dismutation of arylene phosphorodiamidites: Specific features and aspects of preparative use

The dismutation of arylene phosphorodiamidites derived from the simplest phenols and naphthols and of their dibasic analogs was studied. The main regular trends of this process and the limits of its synthetic applicability were determined. Pleiades Publishing, Inc., 2006.

Dismutation of diamidoarylphosphites

Some examples of spontaneous dismutation of diamidoarylphosphites in different solvents were studied, and features of the process were revealed.

A simple Preparation of 5'-O-dimethoxytrityl Deoxyribonucleoside 3'-O-Phosphorbisdiethylamidites as Useful Intermediates in the Synthesis of Oligodeoxyribonucleotides and Their Phosphorodiethylamidate Analogs on a Solid Support

5'-O-Dimethoxytrityl deoxyribonucleoside 3'-O-phosphorbisdiethylamidites were prepared by the selective phosphitylation of 5'-O-dimethoxytrityl deoxyribonucleosides with tris(diethylamino)phosphine in the presence of amine and tetrazol as catalyst.The bisamidites activated by p-nitrophenyltetrazole can be coupled efficiently with 5'hydroxyl group of nucleoside on a solid support.Oligodeoxyribonucleotides were obtined in high yields.The phosphorodiethylamidate linkage was obtained by non-aqueous oxidation using tert-butyl hydroperoxyde of the phosphordiethylamidite formed after the coupling.

A CONVENIENT AND HIGH YIELD SYNTHESIS OF TERTIARY (AMINO) PHOSPHINES BY TRANSAMINATION ROUTE

Tris(diethylamino)phosphine affords tertiary (amino) phosphines of pyrrolidine, piperidine, hexamethyleneimine, morpholine and N-methylpiperazine in nearly quantitative yields by transamination route - an easy and convenient synthesis occuring under mild conditions.

AMIDATION OF HALOGEN DERIVATIVES OF PHOSPHORUS WITH 4,4',4''-METHYLIDYNETRISMORPHOLINE

4,4'4''-Methylidynetrismorpholine amidates polyhalophosphorus compounds and is a more reactive agent than the previously studied N,N,N'N'-tetraalkylmethanediamines.The dimorpholinomethylium chloride formed as a result of the reaction does not react with the amidation products, which makes it possible to isolate them in a pure state.

Desulfurization of Organic Trisulfides by Tris(dialkylamino)phosphines. Mechanistic Aspects

Tris(dialkylamino)phosphines effect a rapid desulfurization of trisulfides to disulfides under mild conditions.The reaction mechanism involves a bimolecular process, proceeding by the rate-determining formation of a phosphonium salt intermediate.The central sulfur atom of a diaryl trisulfide is removed in the process, while a dialkyl trisulfide loses a terminal sulfur atom to the aminophosphine.