797-70-6

Basic information

• Product Name: TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE
• Synonyms: tris(p-tolyl)-phosphineoxid;tris(p-tolyl)phosphineoxide;TRI-P-TOLYLPHOSPHINE OXIDE;TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE;Trismethylphenylphosphineoxide;1-bis(4-methylphenyl)phosphoryl-4-methylbenzene;1-bis(4-methylphenyl)phosphoryl-4-methyl-benzene
• CAS NO: 797-70-6
• Molecular Formula: C₂₁H₂₁OP
• Molecular Weight: 320.36
• Mol File: 797-70-6.mol
• Article Data: 47

Chemical Properties

• Melting Point: 145 °C
• Boiling Point: 490 °C at 760 mmHg
• Flash Point: 250.2 °C
• Appearance: /
• Density: 1.12 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE(797-70-6)
• EPA Substance Registry System: TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE(797-70-6)

Safety Data

• RTECS: SZ2000000
• Hazardous Substances Data: 797-70-6(Hazardous Substances Data)

Usage

General Description

TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE is a chemical compound with the molecular formula C21H21OP. It is a phosphine oxide derivative used as a ligand in various catalytic processes, particularly in the field of organic synthesis. It is also utilized as a stabilizing agent for radical species in organic chemistry reactions. TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE is known for its ability to form strong coordination bonds with metal ions, making it a valuable tool in the development of new catalysts for organic transformations. TRIS(4-METHYLPHENYL)PHOSPHINE OXIDE has found applications in a wide range of fields, including pharmaceuticals, polymers, and materials science.

Upstream product

• 1038-95-5 Tri(p-tolyl)phosphine 
• 61249-20-5 Methyl-tri-p-tolyl-phosphonium 
• 7726-95-6 bromine 
• 106-38-7 para-bromotoluene 
• 2409-61-2 di(p-tolyl)phosphine oxide 
• 93131-73-8 4-tolyl perfluorobutanesulfonate 
• 106-44-5 p-cresol 
• 29540-83-8 p-tolyl triflate 
• 624-31-7 4-tolyl iodide 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 603-35-0 triphenylphosphine 
• 152386-96-4 oxotrimesityliridium(V) 
• 7175-54-4 cumyl peroxy radical 

Downstream Products

• 807-19-2 4,4,4-phosphoryltribenzoic acid 
• 84191-05-9 [Rh(CO)2(OP(CH₃C₆H₄)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh(CO)2(OP(CH₃C₆H₄)3)2]ClO₄ 
• 105071-37-2 tris(p-tolyl)phosphine borane complex 
• 1449430-72-1 (E)-[2-(1,2-diphenylethenyl)-4-methylphenyl]bis(4-methylphenyl)phosphine oxide 
• 84190-63-6 [Rh(CO)(OP(CH₃C₆H₄)3)(P(C₆H₅)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh(CO)(OP(CH₃C₆H₄)3)(P(C₆H₅)3)2]ClO₄ 
• 1038-95-5 Tri(p-tolyl)phosphine 
• 21859-00-7 tri(p-tolyl)phosphine dichloride 
• 84190-87-4 [Rh((CHCHC₂H₄)2)(OP(CH₃C₆H₄)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh((CHCHC₂H₄)2)(OP(CH₃C₆H₄)3)2]ClO₄ 
• 133192-00-4 N-phenyl-P,P,P-trisphospha-λ⁵-azene 

Relevant articles and documents

Conversion from Heterometallic to Homometallic Metal–Organic Frameworks

Two new heterometallic metal–organic frameworks (MOFs), LnZnTPO 1 and 2, and two homometallic MOFs, LnTPO 3 and 4 (Ln=Eu for 1 and 3, and Tb for 2 and 4; H3TPO=tris(4-carboxyphenyl)phosphine oxide) were synthesized, and their structures and pro

A Mononuclear Non-Heme Manganese(III)-Aqua Complex in Oxygen Atom Transfer Reactions via Electron Transfer

Metal-oxygen complexes, such as metal-oxo [M(O2-)], -hydroxo [M(OH-)], -peroxo [M(O22-)], -hydroperoxo [M(OOH-)], and -superoxo [M(O2?-)] species, are capable of conducting oxygen atom transfer (OAT) reactions with organic substrates, such as thioanisole (PhSMe) and triphenylphosphine (Ph3P). However, OAT of metal-aqua complexes, [M(OH2)]n+, has yet to be reported. We report herein OAT of a mononuclear non-heme Mn(III)-aqua complex, [(dpaq)MnIII(OH2)]2+ (1, dpaq = 2-[bis(pyridin-2-ylmethyl)]amino-N-quinolin-8-yl-acetamidate), to PhSMe and Ph3P derivatives for the first time; it is noted that no OAT occurs from the corresponding Mn(III)-hydroxo complex, [(dpaq)MnIII(OH)]+ (2), to the substrates. Mechanistic studies reveal that OAT reaction of 1 occurs via electron transfer from 4-methoxythioanisole to 1 to produce the 4-methoxythioanisole radical cation and [(dpaq)MnII(OH2)]+, followed by nucleophilic attack of H2O in [(dpaq)MnII(OH2)]+ to the 4-methoxythioanisole radical cation to produce an OH adduct radical, 2,4-(MeO)2C6H3S?(OH)Me, which disproportionates or undergoes electron transfer to 1 to yield methyl 4-methoxyphenyl sulfoxide. Formation of the thioanisole radical cation derivatives is detected by the stopped-flow transient absorption measurements in OAT from 1 to 2,4-dimethoxythioanisole and 3,4-dimethoxythioanisole, being compared with that in the photoinduced electron transfer oxidation of PhSMe derivatives, which are detected by laser-induced transient absorption measurements. Similarly, OAT from 1 to Ph3P occurs via electron transfer from Ph3P to 1, and the proton effect on the reaction rate has been discussed. The rate constants of electron transfer from electron donors, including PhSMe and Ph3P derivatives, to 1 are fitted well by the electron transfer driving force dependence of the rate constants predicted by the Marcus theory of outer-sphere electron transfer.

Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

An iodide-accelerated, palladium-catalyzed C-P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C-P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.