4576-56-1

Basic information

• Product Name: Tri(4-chlorophenyl)phosphine oxide
• Synonyms: Tri(4-chlorophenyl)phosphine oxide
• CAS NO: 4576-56-1
• Molecular Formula: C₁₈H₁₂Cl₃OP
• Molecular Weight: 381.620041
• Mol File: 4576-56-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 524°Cat760mmHg
• Flash Point: 270.7°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.5E-10mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: Tri(4-chlorophenyl)phosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Tri(4-chlorophenyl)phosphine oxide(4576-56-1)
• EPA Substance Registry System: Tri(4-chlorophenyl)phosphine oxide(4576-56-1)

Safety Data

• Hazardous Substances Data: 4576-56-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H12Cl3OP/c19-13-1-7-16(8-2-13)23(22,17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 1159-54-2 tri(4-chlorophenyl)phosphine 
• 35856-82-7 3,3,4,4-tetramethyl-1,2-dioxetane 
• 6133-92-2 4-Phenyl-1,2-dithiolane 
• 7664-93-9 sulfuric acid 
• 5032-62-2 tris-p-chlorophenylphosphine sulphide 
• 106-39-8 bromochlorobenzene 
• 152386-96-4 oxotrimesityliridium(V) 
• 15676-97-8 Tris-(4-chlor-phenyl)-ethoxy-carbonylmethylen-phosphoran-hydrobromid 
• 7175-54-4 cumyl peroxy radical 
• 124-64-1 tetrakis(hydroxymethyl)phosphonium chloride 
• 3400-27-9 2-methyl-3-p-nitrophenyloxaziridine 
• 73116-94-6 2,2,2-Tris-(4-chloro-phenyl)-4,4,5,5-tetramethyl-2λ⁵-[1,3,2]dioxaphospholane 

Downstream Products

• 1449430-74-3 (E)-[4-chloro-2-(1,2-diphenylethenyl)phenyl]bis(4-chlorophenyl)phosphine oxide 
• 84190-59-0 [Rh(CO)(OP(ClC₆H₄)3)(P(C₆H₅)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh(CO)(OP(ClC₆H₄)3)(P(C₆H₅)3)2]ClO₄ 
• 84214-29-9 [Rh(CO)2(OP(ClC₆H₄)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh(CO)2(OP(ClC₆H₄)3)2]ClO₄ 
• 1159-54-2 tri(4-chlorophenyl)phosphine 

Relevant articles and documents

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.

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.

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.