6163-63-9

Basic information

• Product Name: tris(2-methylphenyl)phosphane oxide
• Synonyms: Tri-O-tolylphosphine oxide
• CAS NO: 6163-63-9
• Molecular Formula: C₂₁H₂₁OP
• Molecular Weight: 320.3646
• Mol File: 6163-63-9.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 504.4°C at 760 mmHg
• Flash Point: 258.8°C
• Density: 1.12g/cm³
• Vapor Pressure: 8.4E-10mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: tris(2-methylphenyl)phosphane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: tris(2-methylphenyl)phosphane oxide(6163-63-9)
• EPA Substance Registry System: tris(2-methylphenyl)phosphane oxide(6163-63-9)

Safety Data

• Hazardous Substances Data: 6163-63-9(Hazardous Substances Data)

Usage

General Description

Tris(2-methylphenyl)phosphane oxide, also known as TMPP oxide, is a chemical compound with the formula (C6H4CH3)3PO. It is a phosphorus-based compound that is commonly used as a flame retardant and as a stabilizer in the production of polyurethane foam. TMPP oxide is also used as a reactive diluent in epoxy resins and as a catalyst in various chemical reactions. It is a white crystalline solid that is insoluble in water but soluble in organic solvents. TMPP oxide is considered to be relatively non-toxic and non-hazardous, but as with any chemical, proper handling and storage procedures should be followed to ensure safety.

Upstream product

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

Downstream Products

• 1366181-68-1 [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OP(o-tolyl)3)] 
• 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 
• 30309-80-9 di-o-tolylphosphine oxide 

Relevant articles and documents

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 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.).

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}.