6163-63-9

Usage

Uses

Used in Flame Retardants:
TMPP oxide is used as a flame retardant in various applications to reduce the flammability of materials and improve their fire safety. It is particularly effective in polymers and plastics, where it can help to slow down the spread of flames and reduce the release of toxic gases during combustion.
Used in Polyurethane Foam Production:
In the production of polyurethane foam, TMPP oxide is used as a stabilizer to control the reaction rate and improve the physical properties of the final product. It helps to achieve a more uniform cell structure and better mechanical properties, such as tensile strength and elongation at break.
Used as a Reactive Diluent in Epoxy Resins:
TMPP oxide is used as a reactive diluent in epoxy resins to reduce the viscosity of the resin and improve its processability. It can also enhance the curing properties and mechanical performance of the final product, making it suitable for applications such as coatings, adhesives, and composite materials.
Used as a Catalyst in Chemical Reactions:
TMPP oxide is employed as a catalyst in various chemical reactions, including polymerization, esterification, and transesterification processes. Its ability to accelerate reaction rates and improve product yields makes it a valuable component in the synthesis of various chemicals and materials.
Used in Coatings and Adhesives:
TMPP oxide is used in the formulation of coatings and adhesives to improve their performance characteristics, such as adhesion, flexibility, and chemical resistance. Its presence in these formulations can also contribute to enhanced flame retardancy and thermal stability.
Used in Composite Materials:
In composite materials, TMPP oxide can be used to improve the interfacial adhesion between the matrix and the reinforcing fibers, leading to enhanced mechanical properties and durability. Its flame retardant properties can also be beneficial in applications where fire resistance is a critical requirement.

Upstream product

• 64-17-5 ethanol 
• 127-65-1 chloroamine-T 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 1366181-68-1 [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OP(o-tolyl)3)] 
• 75-05-8 acetonitrile 
• 152386-96-4 oxotrimesityliridium(V) 

Downstream Products

• 1366181-68-1 [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OP(o-tolyl)3)] 
• 30309-80-9 di-o-tolylphosphine oxide 
• 1449430-79-8 (E)-[2-(1,2-diphenylethenyl)-6-methylphenyl]bis(2-methylphenyl)phosphine oxide 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 156813-99-9 tri-o-tolylphosphonium chloride 

Relevant academic research and scientific papers

Di(hydroperoxy)cycloalkane Adducts of Triarylphosphine Oxides: A Comprehensive Study including Solid-State Structures and Association in Solution

Four new di(hydroperoxy)cycloalkane adducts (Ahn adducts) of p-Tol3PO (1) and o-Tol3PO (2), namely, p-Tol3PO·(HOO)2C(CH2)5 (3), o-Tol3PO·(HOO)2C(CH2)5 (4), p-Tol3PO·(HOO)2C(CH2)6 (5), and o-Tol3PO·(HOO)2C(CH2)6 (6), have been synthesized and fully characterized. Their single crystal X-ray structures have been determined and analyzed. The 31P NMR data are in accordance with hydrogen bonding of the di(hydroperoxy)alkanes to the P═O groups of the phosphine oxides. Due to their high solubility in organic solvents, natural abundance 17O NMR spectra of 1-6 could be recorded, providing the signals for the P═O groups and additionally the two different oxygen nuclei in the O-OH groups in the adducts 3-6. The association and mobility of 3-6 were explored by 1H DOSY (diffusion ordered spectroscopy) NMR, which indicated persistent hydrogen bonding of the adducts in solution. Competition experiments with phosphine oxides allowed ranking of the affinities of the di(hydroperoxy)cycloalkanes for the different phosphine oxide carriers. On the basis of variable temperature 31P NMR investigations, the Gibbs energies of activation ΔG? for the adduct dissociation processes of 3-6 at different temperatures, as well as the enthalpy ΔH? and entropy ΔS? of activation, have been determined. IR spectroscopy of 3-6 corroborated the hydrogen bonding, and in the Raman spectra, the ν(O-O) stretching bands have been identified, confirming the presence of peroxy groups in the solid materials. The high solubilities in selected organic solvents have been quantified.

The Impact of Solvent Quality on the Heck Reaction: Detection of Hydroperoxide in 1-Methyl-2-pyrrolidinone (NMP)

Unexpected failures of a Heck reaction in the lab led to the detection of 5-hydroperoxy-1-methyl-2-pyrrolidinone (NMP-5-OOH) in the cosolvent 1-methyl-2-pyrrolidinone (NMP). This hydroperoxide, formed by autoxidation in the presence of air, oxidized the ligand tri(o-tolyl)phosphine (P(o-tol)3) to tri(o-tolyl)phosphine oxide (O═P(o-tol)3) and ultimately slowed down the Heck reaction. Because of this finding, control strategies were implemented for NMP quality and air exclusion during manufacturing campaigns, which ensured delivery of metric tons of compound 2 en route to Ronacaleret Hydrochloride used in clinical studies. Similar detrimental impact of NMP-5-OOH to the ligand-free Heck reaction was also demonstrated.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Air-stable phosphine organocatalysts for the hydroarsination reaction

Readily-available triarylphosphines are explored as organocatalysts for the hydroarsination reaction. When compared to transition metal catalysis, phosphine organocatalysis greatly improved solvent compatibility of the hydroarsination of nitrostyrenes. Upon complete conversion, arsine products were isolated in up to 99% yield while up to 48% of the phosphine catalyst was still active. A mechanism was proposed and structure-activity analysis regarding catalyst activity concluded that sterically-bulkier catalysts were effective at minimizing catalyst deactivation.

EUROPIUM COMPLEX

To provide europium complexes having high photostability. A europium complex expressed with the following formula (A): {wherein, RA and RB are independently a cyclic alkyl group with 3 to 10 carbons, respectively, and RC is a cyclic alkyl group with 3 to 10 carbons or a phenyl group expressed with the following formula (B): (wherein, XA, XB, AC, XD and XE independently represent a hydrogen atom; a fluorine atom; an alkyl group with 1 to 3 carbon(s); an alkyloxy group with 1 to 3 carbon(s); an aryloxy group with 6 to 10 carbons; a fluoroalkyl group with 1 to 3 carbon(s); a fluoroalkyloxy group with 1 to 3 carbon(s); or a phenyl group that may be substituted with a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a fluorophenyl group, a hydroxyl group or a cyano group, respectively); RA is a cyclic alkyl group with 3 to 10 carbons; RB and RC are a phenyl group expressed with the formula (B), provided, however, that a case where RA a cyclohexyl group, and, RB and RC are a phenyl group is excluded; or RA, RB and RC independently represent an ortho-substituted phenyl group expressed with the following formula (Ba): (wherein, XE represents a hydrogen atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a naphthyl group that may be substituted with a fluorine atom, a pyridyl group that may be substituted with a fluorine atom, or a phenyl group that is expressed with a formula (C): [wherein, ZA, ZC and ZE independently represent a hydrogen atom, a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a phenyl group that may be substituted with a fluorine atom, a hydroxyl group or a cyano group; ZB and ZD independently represent a hydrogen atom or a fluorine atom, respectively], provided, however, that a case where RA, RB and RC are all a phenyl group is excluded), respectively; RD represents a hydrogen atom, a deuterium atom or a fluorine atom; WA and WB independently represent an alkyl group with 1 to 6 carbon(s), a fluoroalkyl group with 1 to 6 carbon(s), a phenyl group, a 2-thienyl group or a 3-thienyl group; and ‘n’ represents an integer of 1 to 3}.

Visible light-induced 4-phenylthioxanthone-catalyzed aerobic oxidation of triarylphosphines

We report herein a visible light-induced oxidation of triarylphosphines under aerobic condition with excellent functional group tolerance. In this transformation, the photo catalyst 4-phenylthioxanthone acted as a photosensitizer for the in situ generation of singlet oxygen. This new approach provided a cheaper and greener method for the preparation of phosphine oxide, showing great advantages in environmental protocols.

Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen

The metal-free reduction of phosphane oxides with molecular hydrogen (H2) using oxalyl chloride as activating agent was achieved. Quantum-mechanical investigations support the heterolytic splitting of H2 by the in situ formed electrophilic phosphonium cation (EPC) and phosphane oxide and subsequent barrierless conversion to the phosphane and HCl. The reaction can also be catalyzed by the frustrated Lewis pair (FLP) consisting of B(2,6-F2C6H3)3 and 2,6-lutidine or phosphane oxide as Lewis base. This novel reduction was demonstrated for triaryl and diaryl phosphane oxides providing access to phosphanes in good to excellent yields (51–93 %).

A new method to prepare functional phosphines through steady-state photolysis of triarylphosphines

The steady-state photolysis of triarylphosphine, Ar3P, was carried out using a xenon lamp or a high-pressure mercury lamp under an argon atmosphere in a solvent containing a functional group, CH3X. Gas chromatograph-mass spectroscopic analysis on the photolysis showed that a phosphine to which the functional group from the solvent is incorporated, Ar2PCH2X, was formed in a moderate yield, along with tetraaryldiphosphine, Ar2PPAr2. The product, Ar2PCH2CN, from the photolysis in acetonitrile (X=CN) was isolated by column chromatography. In the photolysis in other solvents tried here (ethyl acetate, acetone, 2-butanone, and 3,3-dimethyl-2-butanone), Ar2PCH2X formed in the reaction mixture was so labile on a silica-gel column that it was treated with S8 powder to convert to the corresponding phosphine sulfide, Ar2P(=S)CH2X. The resulting phosphine sulfide was isolated by column chromatography. The isolated products in these reactions, Ar2PCH2CN and Ar2P(=S)CH2X, were characterized by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and elemental analysis or high-resolution mass spectroscopy. The formation of Ar2PCH2X as well as Ar2PPAr2 is explained by homolytic cleavage of a P-C bond of Ar3P in the photoexcited state. This reactivity of Ar3P in the photoexcited state is in sharp contrast to that exerted under aerobic conditions, where Ar3P in the photoexcited state donates readily an electron to oxygen producing the radical cation, Ar3P·+. This photoreaction, which affords a functional phosphine, Ar2PCH2X, in one-pot with generating very small amounts of unidentified side products, has potential for use in preparing functional phosphines.

Eosin Y-catalyzed photooxidation of triarylphosphines under visible light irradiation and aerobic conditions

We report herein a novel method for Eosin Y-catalyzed photooxidation of triarylphosphines under visible light irradiation and aerobic conditions. This new approach employed visible light as the energy source and air as the oxidant, showing great advantages in environmental benignness and operational easiness with a wide functional group tolerance.

Direct oxygen atom transfer versus electron transfer mechanisms in the phosphine oxidation by nonheme Mn(IV)-oxo complexes

Direct oxygen atom transfer from a nonheme Mn(iv)-oxo complex, [(Bn-TPEN)MnIV(O)]2+, to triphenylphosphine (Ph3P) derivatives occurs with a significant steric effect resulting from the ortho-substituents on the phenyl group of the Ph3P derivatives, whereas the phosphine oxygenation by a Mn(iv)-oxo complex in the presence of HOTf occurs via an electron transfer mechanism without the substrate-steric effect.