638-21-1

Usage

Uses

Used in Chemical Synthesis:
Phenyl phosphine is used as a precursor to other organophosphorus compounds, which are important in various chemical reactions and processes. It can function as a ligand in coordination chemistry, playing a crucial role in the formation of metal complexes and their applications.
Used in Suzuki Reaction:
Phenyl phosphine is used as a reagent in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows the formation of carbon-carbon bonds between an organoboron compound and an organohalide, leading to the synthesis of various organic compounds.
Used in Polymer Synthesis:
Phenyl phosphine is used in the synthesis of polymers, where it can act as a monomer or a catalyst to facilitate the polymerization process. Its presence in the polymer structure can impart specific properties, such as improved thermal stability or enhanced reactivity.
Used in Catalysts and Antioxidants:
Phenyl phosphine is used in the production of phenylphosphinates, which serve as catalysts and antioxidants in various industrial applications. When heated above 200°C, phenylphosphinates can yield phenylphosphonic acid derivatives and phenylphosphine, which can be further utilized in different chemical processes.

Air & Water Reactions

Pyrophoric in air. Insoluble in water. Slowly generates flammable or noxious gases in contact with water.

Reactivity Profile

Phenyl phosphine is a reducing agent. They slowly generate flammable or noxious gases in contact with water. Phosphides react quickly upon contact with moisture or acids to give the very toxic gas phosphine; phosphides also can react vigorously with oxidizing materials. In general, materials in this group are incompatible with oxidizers such as atmospheric oxygen. They are violently incompatible with acids, particularly oxidizing acids.

Health Hazard

Phenylphosphine is a respiratory and skin irritant; multiple exposures in rodents causes hematologic changes and testicular degeneration in males.

Fire Hazard

Flash point data are not available for Phenyl phosphine, but Phenyl phosphine is probably combustible.

Safety Profile

Poison by inhalation. Igmtes spontaneously in air. When heated to decomposition it emits toxic fumes of POx. See also PHOSPHINE.

Potential Exposure

Polyphosphinate is used as an intermediate or a chemical reagent. Polyphosphinate compounds are used as catalysts and antioxidants disproportionate, when heated to give phosphonic acid derivatives plus PF.

Shipping

UN2845 Pyrophoric liquids, organic, n.o.s Hazard Class: 4.2, Labels: 4.2-Spontaneously combustible material. Technical Name Required. Note: this chemical is also a strong reducing agent.

Incompatibilities

A strong reducing agent. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Water reactive; spontaneously combustible in high concentrations in moist air. Potential exposure to gaseous phenylphosphine and phosphorus oxides when heated above 200C. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrideds and active metals. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

InChI:InChI=1/C6H7P/c7-6-4-2-1-3-5-6/h1-5H,7H2

Upstream product

• 64-17-5 ethanol 
• 644-97-3 Dichlorophenylphosphine 
• 67-56-1 methanol 
• 89865-20-3 (1-Methoxy-1-phenylphosphanyl-ethyl)-dimethyl-amine 
• 77861-57-5 9-phenyl-9-phosphatricyclo<4.2.1.0^2,5>nona-3,7-diene 
• 90682-77-2 1,2-Diphenyl-3,10-bis(trimethylsiloxy)-1,2-diphospha-3,9-cyclodecadien 
• 1486-37-9 phenyl-dithiophosphonous acid diethyl ester 
• 75-54-7 Dichloromethylsilane 
• 603-35-0 triphenylphosphine 
• 3376-52-1 pentaphenylcyclopentaphosphane 
• 28240-64-4 bis(diphenylphosphino)methane 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 1754-49-0 diethyl phenylphosphonate 

Downstream Products

• 2176-06-9 diphenyldiphosphene 
• 23743-22-8 P,P'-diethyl-P,P'-diphenyl-P,P'-ethanediyl-di-phosphine 
• 2468-05-5 di-(3-hydroxypropyl)-phenyl-phosphin 
• 15909-92-9 bis(2-cyanoethyl)phenylphosphine 
• 6798-66-9 β cyanethyl phenyl phosphin 
• 6775-11-7 bis(2-(carbomethoxy)ethyl)phenylphosphine 
• 6775-06-0 2,2'-dimethyl-3,3'-phenylphosphanediyl-bis-propionic acid dimethyl ester 
• 105838-39-9 (2-ethoxy-ethyl)-ethyl-phenyl-phosphine 
• 109654-15-1 ethyl-(2-methoxymethyl-benzyl)-phenyl-phosphine 
• 10251-55-5 butyl(phenyl)phosphine 
• 350-58-3 phenyl-(1,1,2,2-tetrafluoro-ethyl)-phosphine 
• 789-00-4 phenyl-bis-(1,1,2,2-tetrafluoro-ethyl)-phosphine 
• 67326-29-8 1,4-diphenyl-[1,4]azaphosphinane 
• 109128-36-1 2-phenyl-2,3-dihydro-1H-isophosphindole 

Relevant academic research and scientific papers

PHOSPHORANES BICYCLIQUES A LIAISON P-H : BASES DE LEWIS POTENTIELLES

By reaction of Borane Dimethyl Sulfide on the bicyclophosphorane 1 the adduct 2 is obtained with 56 percent yield; by-products 3 and 4 are characterized.

Can a pentamethylcyclopentadienyl ligand act as a proton-relay in f-element chemistry? Insights from a joint experimental/theoretical study

Isomerisation of buta-1,2-diene to but-2-yne by (Me5C5)2Yb is a thermodynamically favourable reaction, with the ΔrG°estimated from experimental data at 298 K to be -3.0 kcal mol-1. It proceeds in hydrocarbon solvents with a pseudo first-order rate constant of 6.4 × 10-6 s-1 and 7.4 × 10-5 s-1 in C6D12 and C6D6, respectively, at 20°C. This 1,3-hydrogen shift is formally forbidden by symmetry and has to occur by an alternative pathway. The proposed mechanism for buta-1,2-diene to but-2-yne isomerisation by (Me5C5)2Yb involves coordination of methylallene (buta-1,2-diene) to (Me5C5)2Yb, and deprotonation of methylallene by one of the Me5C5 ligands followed by protonation of the terminal methylallenyl carbon to yield the known coordination compound (Me5C5)2Yb(η2-MeCCMe). Computationally, this mechanism is not initiated by a single electron transfer step, and the ytterbium retains its oxidation state (II) throughout the reactivity. Experimentally, the influence of the metal centre is discussed by comparison with the reaction of (Me5C5)2Ca towards buta-1,2-diene, and (Me5C5)2Yb with ethylene. The mechanism by which the Me5C5 acts as a proton-relay within the coordination sphere of a metal also rationalises the reactivity of (i) (Me5C5)2Eu(OEt2) with phenylacetylene, (ii) (Me5C5)2Yb(OEt2) with phenylphosphine and (iii) (Me5C5)2U(NPh)2 with H2 to yield (Me5C5)2U(HNPh)2. In the latter case, the computed mechanism is the heterolytic activation of H2 by (Me5C5)2U(NPh)2 to yield (Me5C5)2U(H)(HNPh)(NPh), followed by a hydrogen transfer from uranium back to the imido nitrogen atom using one Me5C5 ligand as a proton-relay. The overall mechanism by which hydrogen shifts using a pentamethylcyclopentadienyl ligand as a proton-relay is named Carambole in reference to carom billiards.

Photocatalytic Arylation of P4 and PH3: Reaction Development Through Mechanistic Insight

Detailed 31P{1H} NMR spectroscopic investigations provide deeper insight into the complex, multi-step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P4). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non-innocent behavior of the commonly employed terminal reductant Et3N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)2][PF6] (dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine) and 3DPAFIPN. Inspired by the observation of PH3 as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P4 arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.

Process for preparation of phosphorane and phosphonyl compounds

The invention relates to the field of new materials of fine chemicals, in particular to a new safe, convenient, mild, efficient, environment-friendly and economical preparation process technology of phosphorane and phosphonyl compounds.

One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP

Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.

Oligodentate Phosphine Ligands with Phospholane End Groups: New Synthetic Access and Application to Molybdenum-Based Synthetic Nitrogen Fixation

A new synthetic access to oligodentate phosphine ligands with phospholane end groups, starting from lithium phospholanide, is established. Based on this building block, the tridentate ligand prPP(Ph)P-pln was synthesized and used for the synthesis of [MoX3{prPP(Ph)P-pln}] (X = Cl, Br, I) precursors. Sodium amalgam reduction in the presence of N2 and either mono- or bidentate ligands leads to several molybdenum(0) mono- and bis(dinitrogen) complexes, respectively. With the diphosphine dppm a mixture of facial and meridional isomers of [Mo(N2){prPP(Ph)P-pln}(dppm)] is formed. Using the monophosphines PMePh2 and PMe2Ph mer-[Mo(N2){prPP(Ph)P-pln}(PMe2Ph)2] and trans-[Mo(N2)2{prPP(Ph)P-pln}(PMePh2)] could be obtained. The spectroscopic properties and reactivity of the latter towards protonation was investigated, and a hydrazido complex could be obtained and characterized.

Tailoring Phospholes for Imprint of Fluorescent 3D Structures

PMMA based polymer blends have been infused with luminescent phospholes and have been structured via nanoimprint. While symmetrically substituted phospholes are prone to crystallization and phase separation, structural modification of the phosphole backbone in the α- and β-positions has been explored, which prevents these issues; a structural explanation for this is suggested. Best phase integrity has been obtained for β-silyl-substituted phospholes, which were implemented in thin films and beads. The emission wavelengths of the phospholes are shifted bathochromically in the polymer matrix as compared to the neat compounds featuring emission bands near 500 nm. This enables tracking of the fluorescent beads using standard fluorescence microscopy.

Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus(iii) dication under mild conditions

The readily-accessible, air-stable Lewis acid [(terpy)PPh][B(C6F5)4]21 is shown to mediate the hydrosilylation of aldehydes, ketones, and olefins. The utility and mechanism of these hydrosilylations are considered.

Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes

Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P-P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)-Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into the competing mechanisms involved.

Copper-Phosphido Intermediates in Cu(IPr)-Catalyzed Synthesis of 1-Phosphapyracenes via Tandem Alkylation/Arylation of Primary Phosphines

Tandem alkylation/arylation of primary phosphines PH2R (R = Ph, Cy, Fc, FcCH2; Fc = ferrocenyl) with 5-bromo-6-chloromethylacenaphthene (1) and 2 equiv of NaOSiMe3 using the catalyst precursor Cu(IPr)(Cl) gave a series of 1-phosphapyracenes (R-PyraPhos, 2a-d), which were isolated as borane adducts 3a-d. Similar reactions of the chiral air-stable primary phosphines PH2Ar? (Ar? = (S)-binaphthyl (4), (R)-MeO-binaphthyl (5)) to yield 2e,f and 3e,f were diastereoselective (dr = 2:1 and 1.2:1, respectively), and chromatography gave a highly enriched sample of one diastereomer of 3f. The mechanism of catalysis was investigated by NMR monitoring and independent syntheses of potential intermediates. The phosphido complexes Cu(IPr)(PHAr′) (Ar′ = Ph, (R)-MeO-binaphthyl) were generated in equilibrium mixtures, along with Me3SiOH, from Cu(IPr)(OSiMe3) and PH2Ar′. They reacted with benzyl chloride 1 to yield Cu(IPr)(Cl) and the secondary phosphines PHAr′(CH2Ar) (Ar = Br-acenaphthyl); addition of NaOSiMe3 yielded PyraPhos derivatives 2a,f. Deprotonation of the cations [Cu(IPr)(PHAr′CH2Ar)][OTf] (Ar′ = Ph, (R)-MeO-binaphthyl) was investigated as a route to the secondary phosphido complexes Cu(IPr)(PAr′CH2Ar) (13). We propose that C-Br oxidative addition in the Cu(I)-phosphido intermediates 13 followed by P-C reductive elimination from Cu(III)-phosphido complexes forms the PyraPhos ring, with diastereoselection arising from rapid pyramidal inversion of Cu-phosphido groups.