855-38-9

Basic information

• Product Name: TRIS(4-METHOXYPHENYL)PHOSPHINE
• Synonyms: Phosphine, tris(p-methoxyphenyl)-;Phosphorus tri-(p-methoxyphenyl);Tri(p-methoxyphenyl)phosphine;Trianisylphosphine;Tri-p-anisylphosphine;LABOTEST-BB LTBB005439;TRIS(P-ANISYL)PHOSPHINE;TRIS(P-METHOXYPHENYL)PHOSPHINE
• CAS NO: 855-38-9
• Molecular Formula: C₂₁H₂₁O₃P
• Molecular Weight: 352.36
• EINECS: 212-723-0
• Product Categories: Ligand;Phosphine Ligands;Synthetic Organic Chemistry;Basic Phosphine LigandsCatalysis and Inorganic Chemistry;Catalysis and Inorganic Chemistry;Cross-Coupling;Phosphine Ligands;Phosphorus Compounds;organophosphine ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 855-38-9.mol

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 457.8 °C at 760 mmHg
• Flash Point: 287.3 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.1352 (estimate)
• Vapor Pressure: 3.93E-08mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 2815911
• CAS DataBase Reference: TRIS(4-METHOXYPHENYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(4-METHOXYPHENYL)PHOSPHINE(855-38-9)
• EPA Substance Registry System: TRIS(4-METHOXYPHENYL)PHOSPHINE(855-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 855-38-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRIS(4-METHOXYPHENYL)PHOSPHINE is used as a reagent and intermediate in organic synthesis for various applications, such as the formation of carbon-carbon and carbon-heteroatom bonds. Its phosphine functionality allows it to act as a nucleophile or a reducing agent, making it suitable for a wide range of reactions.
Used in the Suzuki Reaction:
In the field of cross-coupling reactions, TRIS(4-METHOXYPHENYL)PHOSPHINE is used as a key component in the Suzuki reaction. This reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds, which are important structural motifs in pharmaceuticals, agrochemicals, and materials science. The Suzuki reaction involves the coupling of an organoboron compound with an organohalide in the presence of a palladium catalyst and a base, with TRIS(4-METHOXYPHENYL)PHOSPHINE often serving as a ligand to enhance the reaction's efficiency and selectivity.
Used in Other Chemical Processes:
Beyond its applications in organic synthesis and the Suzuki reaction, TRIS(4-METHOXYPHENYL)PHOSPHINE is also employed in other chemical processes. Its unique structure and reactivity make it a valuable intermediate for the development of new synthetic methods, catalysts, and materials. Its applications can be found across various industries, including pharmaceuticals, agrochemicals, and materials science, where it contributes to the advancement of new compounds and technologies.

InChI:InChI=1/C21H21O3P/c1-22-16-4-10-19(11-5-16)25(20-12-6-17(23-2)7-13-20)21-14-8-18(24-3)9-15-21/h4-15H,1-3H3

Synthetic route

Tris(4-methoxyphenyl)phosphine oxide (803-17-8) → P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
With chloro-trimethyl-silane; tetrabutylammomium bromide; copper; zinc In acetonitrile at 45℃; Electrochemical reaction; Inert atmosphere;	93%
With chloro-trimethyl-silane; magnesium at 20℃; for 2h;	93%
With oxalyl dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; triethylamine In dichloromethane at 40℃; for 2h; Inert atmosphere;	83%

1-bromo-4-methoxy-benzene (104-92-7) → P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
With phosphorus trichloride	89%
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran at 42 - 55℃; for 2h; Stage #2: With phosphorus trichloride In tetrahydrofuran at 25 - 85℃; for 3.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1.5h;	75.62%
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.5h; Inert atmosphere; Stage #2: With phosphorus trichloride In tetrahydrofuran; hexane at -50 - -10℃; Inert atmosphere;	55%

(4-methoxyphenyl)zinc(II) bromide (82303-13-7) → P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
With phosphorus trichloride In acetonitrile at 20℃; for 2h;	45%

4-methoxyphenyl magnesium bromide (13139-86-1) → P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
With diethyl ether; hydrogen; phosphorus trichloride

p-methoxyphenyllithium (14774-77-7) → P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
With phosphorus trichloride at -20℃; Yield given;

(2-quinaldinate)(carbonyl)(P(4-CH3O-C5H4)3)2rhodium(I) (119854-20-5) → (2-quinaldinate)(carbonyl)(P(4-CH3O-C5H4)3)rhodium(I) (119882-07-4) + P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
In not given 24 h;

C39H33BF3O3P → P(p-CH3OC6H4)3 (855-38-9) + tris(4-fluorophenyl)borane (47196-74-7)

Conditions	Yield
In dichloromethane at 20℃;

C39H33BCl3O3P → tris(4-chlorophenyl)borane (28445-30-9) + P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
In dichloromethane at 20℃;

C39H27BF9O3P → P(p-CH3OC6H4)3 (855-38-9) + tris(2,4,6-trifluorophenyl)borane triethylphosphine oxide

Conditions	Yield
In dichloromethane at 20℃;

C39H27BF9O3P → tris(3,4,5-trifluorophenyl)borane (148892-97-1) + P(p-CH3OC6H4)3 (855-38-9)

Conditions	Yield
In dichloromethane at 20℃;

P(p-CH3OC6H4)3 (855-38-9) → Tris(4-methoxyphenyl)phosphine oxide (803-17-8)

Conditions	Yield
With 4-phenylthioxanthone In methanol at 20℃; under 760.051 Torr; for 0.666667h; Mechanism; Solvent; Irradiation;	100%
With potassium permanganate	99%
With gold(III) complex supported on cellulose extracted from Carthamus tinctorius immobilized on nanofibrous phosphosilicate; air at 20℃; for 1h; Irradiation;	98%

4-tolyl iodide (624-31-7) + P(p-CH3OC6H4)3 (855-38-9) → Tris-(4-methoxy-phenyl)-p-tolyl-phosphonium; iodide

Conditions	Yield
With palladium diacetate In benzene at 120℃; for 25h;	100%

P(p-CH3OC6H4)3 (855-38-9) → tris(4-methoxyphenyl)phosphine selenide (41398-48-5)

Conditions	Yield
With selenium In toluene for 6h; Heating;	100%
With selenium In toluene at 90℃;	97%
With selenium In ethanol Heating;

[FeI(CO)2(η5-C5H4CH3)] + P(p-CH3OC6H4)3 (855-38-9) → (η5-C5H4Me)Fe(CO)P(p-C6H4OMe)3I + [(η5-C5H4Me)Fe(CO)2P(p-C6H4OMe)3]I (959421-09-1)

Conditions	Yield
di(cyclopentadienideiron dicarbonyl) In neat (no solvent) Fe-compound and P-compound placed in 1:5 molar ratio in agate mortar; gently ground; transferred into NMR tube; placed at 100°C for 15 min; chilled in ice;	A 0% B 100%
In neat (no solvent) Fe-compound and P-compound placed in 1:5 molar ratio in agate mortar; gently ground; transferred into NMR tube; placed at 70°C for 0.5 or4 min; chilled in ice;	A 0% B 100%
di(cyclopentadienideiron dicarbonyl) In neat (no solvent) Fe-compound and P-compound placed in 1:5 molar ratio in agate mortar; gently ground; transferred into NMR tube; placed at 100°C for 5 min; chilled in ice;	A 0% B 84%

P(p-CH3OC6H4)3 (855-38-9) → tris(4-methoxyphenyl)phosphonium tetrafluoroborate

Conditions	Yield
With tetrafluoroboric acid In diethyl ether at 20℃; Inert atmosphere;	100%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + P(p-CH3OC6H4)3 (855-38-9) → (tris(4-methoxyphenyl)phosphine)gold(I) chloride (96029-36-6)

Conditions	Yield
In dichloromethane at 20℃; for 15h; Inert atmosphere;	100%
In dichloromethane at 20℃; for 1h;	63%
In not given addn. of P compd. to Au complex;

P(p-CH3OC6H4)3 (855-38-9) + 7-azido-4-methyl-2H-chromen-2-one → 4-methyl-7-((tris(4-methoxyphenyl)-λ5-phosphanylidene)-amino)-2H-chromen-2-one

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

P(p-CH3OC6H4)3 (855-38-9) + α,α'-dibromo-o-xylene (91-13-4) → (2-(bromomethyl)benzyl)tris(4-methoxyphenyl)phosphonium bromide

Conditions	Yield
In toluene at 20℃; Inert atmosphere; Schlenk technique;	99.5%

chloro(1,5-cyclooctadiene)rhodium(I) dimer + P(p-CH3OC6H4)3 (855-38-9) + 1-adamantyl isocyanide (22110-53-8) → C53H57ClNO6P2Rh

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	99%

P(p-CH3OC6H4)3 (855-38-9) + trimethoxonium tetrafluoroborate (420-37-1) → C22H24O3P(1+)*BF4(1-)

Conditions	Yield
In dichloromethane at 20℃; for 3h; Inert atmosphere;	99%

P(p-CH3OC6H4)3 (855-38-9) + methyl 4-azidotetrafluorobenzoate (122590-75-4) → methyl 2,3,5,6-tetrafluoro-4-((tris(4-methoxyphenyl)-λ5-phosphanylidene)amino)benzoate

Conditions	Yield
at 25℃; for 2h; Kinetics; Inert atmosphere;	99%

P(p-CH3OC6H4)3 (855-38-9) + PtCl(8-O-quinoline)(dmso) → C51H48NO7P2Pt(1+)*Cl(1-)

Conditions	Yield
In chloroform at 60℃; for 24h; Schlenk technique; Inert atmosphere;	99%

P(p-CH3OC6H4)3 (855-38-9) + 3-hydroxy-4-iodopyridine (188057-20-7) → (3-hydroxypyridin-4-yl)tris(4-methoxyphenyl)phosphonium iodide

Conditions	Yield
In chloroform at 50℃; for 19h;	99%

P(p-CH3OC6H4)3 (855-38-9) + 4-iodo-3,5-dimethylpyridine → (3,5-dimethylpyridin-4-yl)tris(4-methoxyphenyl)phosphonium iodide

Conditions	Yield
In chloroform at 80℃; for 19h;	99%

P(p-CH3OC6H4)3 (855-38-9) + 5-bromo-2-chloro-4-iodopyridine (401892-47-5) → (5-bromo-2-chloropyridin-4-yl)tris(4-methoxyphenyl)phosphonium iodide

Conditions	Yield
In chloroform at 80℃; for 19h;	99%

P(p-CH3OC6H4)3 (855-38-9) + 3-(allyloxy)-4-iodopyridine → I(1-)*C29H29NO4P(1+)

Conditions	Yield
In chloroform at 20℃; for 36h;	99%

(1,2,5,6-η4-cycloocta-1,5-diene)bis(4-methoxyphenyl)platinum(II) + P(p-CH3OC6H4)3 (855-38-9) → cis-bis(4-methoxyphenyl)bis{tris(4-methoxyphenyl)phosphane}platinum(II)

Conditions	Yield
In dichloromethane dropping of soln. of phosphane derivative to soln. of Pt complex then stirring at 0°C for 6 h; evapg. of solvent, hydrolysing with ice water, sepg., extg. of aq. layer with C6H6 then CH2Cl2, washing with H2O, drying over MgSO4, evapg. to dryness, dissolving in CH2Cl2 then pptg. with n-hexane; elem. anal.;	98%

allyl(cyclopentadiene)palladium(II) (1271-03-0) + 4-fluoro-1-iodobenzene (352-34-1) + P(p-CH3OC6H4)3 (855-38-9) → (4-fluorophenyl)Pd(P(4-methoxyphenyl)3)2I (180891-50-3)

Conditions	Yield
In dichloromethane Ar-atmosphere; stirring (room temp., 5 - 15 min); filtering (PTFE membrane), crystn. on concg. and hexane addn. (-30°C, overnight), filtering, drying (vac.); elem. anal.;	98%

(η5-cyclopentadienyl)(p-toluenesulfonylimido-kN-thio-kS-ethene-2-thiolato-kS)cobalt(III) + P(p-CH3OC6H4)3 (855-38-9) → C5H5CoS2C2(COOCH3)2NSO2C6H4CH3P(C6H4OCH3)3

Conditions	Yield
In dichloromethane (Ar); stirring a soln. of cobalt complex and phosphine in CH2Cl2 at roomtemp. for 5 min; evapn., column chromy.;	98%

3-Bromopropionic acid (590-92-1) + P(p-CH3OC6H4)3 (855-38-9) → C24H26O5P(1+)*Br(1-) (1394132-29-6)

Conditions	Yield
In toluene for 5h; Reflux;	98%

thallium(I) hexafluorophosphate + (tris(4-methoxyphenyl)phosphine)gold(I) chloride (96029-36-6) + P(p-CH3OC6H4)3 (855-38-9) → [Au{tris((4-methoxyphenyl)phosphine)2}]PF6

Conditions	Yield
In dichloromethane for 1h; Darkness;	98%

3-chloro-4 iodopyridine (77332-79-7) + P(p-CH3OC6H4)3 (855-38-9) → (3-chloropyridin-4-yl)tris(4-methoxyphenyl)phosphonium iodide

Conditions	Yield
In chloroform at 20℃; for 36h;	98%

4-iodopyridin-2-ol + P(p-CH3OC6H4)3 (855-38-9) → tris(4-methoxyphenyl)(2-oxo-1,2-dihydropyridin-4-yl)phosphonium iodide

Conditions	Yield
In chloroform at 50℃; for 19h;	98%

copper(l) iodide (7681-65-4) + P(p-CH3OC6H4)3 (855-38-9) + 2-(bis(4-methylphenyl)phosphino)-4-methylpyridine → (2-(bis(4-methylphenyl)phosphino)-4-methylpyridin)(tris(4-methoxyphenyl)phosphine)2Cu2I2

Conditions	Yield
In dichloromethane at 25℃; for 15h; Inert atmosphere;	98%

allyl(cyclopentadiene)palladium(II) (1271-03-0) + 4-tolyl iodide (624-31-7) + P(p-CH3OC6H4)3 (855-38-9) → (4-methylphenyl)Pd(P(4-methoxyphenyl)3)2I (180891-49-0)

Conditions	Yield
In dichloromethane Ar-atmosphere; stirring (room temp., 5 - 15 min); filtering (PTFE membrane), crystn. on concg. and hexane addn. (-30°C, overnight), filtering, drying (vac.); elem. anal.;	97%

{2-(dimethylaminomethyl)phenyl}(1,10-phenanthroline)gold(III) bis(tetrafluoroborate) + P(p-CH3OC6H4)3 (855-38-9) → {Au((CH3)2NCH2C6H4)(C12H8N2)P(C6H4OCH3)3}(2+)*2{BF4}(1-) = {Au((CH3)2NCH2C6H4)(C12H8N2)P(C6H4OCH3)3}{BF4}2

Conditions	Yield
In dichloromethane solid P(C6H4OMe-p)3 added at room temp.to a suspn. of Au-complex, stirred for 1 h; concd., Et2O added, filtered off, recrystd. from CH2Cl2-Et2O; elem. anal.;	96%

pentacarbonyl[3-(dimethylamino)-3-phenyl-1,2-propadienylidene]chromium + P(p-CH3OC6H4)3 (855-38-9) → cis-tetracarbonyl(3-dimethylamino-3-phenylpropa-1,2-dienylidene)[tris(4-methoxyphenyl)phosphane]chromium

Conditions	Yield
In tetrahydrofuran byproducts: CO; Irradiation (UV/VIS); (Ar); irradn. of a soln. of chromium complex and phosphine in THF at -20°C for 2.5 h; evapn., chromy. (silica gel, pentane/CH2Cl2/THF); elem. anal.;	96%

ferrocenium(III) tetrafluoroborate (1282-37-7) + dichloromethane (75-09-2) + (OC)3Fe((CH2)3S2)Ni(Ph2P(CH2)2PPh2) (877034-21-4, 877034-22-5) + P(p-CH3OC6H4)3 (855-38-9) → [(dppe)Ni(propaneditiolate)Fe(CO)2(P(p-C6H4OMe)3)]BF4*0.25CH2Cl2

Conditions	Yield
With pentane In dichloromethane MBraun glovebox, under N2; soln. of NiFe compd. and FcBF4 in CH2Cl2, rapid stirring for 1 min, above soln. added to phosphine in CH2Cl2, 0.5 min, pentane added (-28°C, then 1 h at this temp.); filtered, washed (pentane, -28°C), dried; elem. anal.;	96%

dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II) (677736-23-1) + P(p-CH3OC6H4)3 (855-38-9) → carbonyl(chloro)(tris(4-methoxyphenyl)phosphine-κP)(η5-pentaphenylcyclopentadienyl)ruthenium(II)

Conditions	Yield
With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique;	96%

Upstream product

• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 14774-77-7 p-methoxyphenyllithium 
• 82303-13-7 (4-methoxyphenyl)zinc(II) bromide 
• 119854-20-5 (2-quinaldinate)(carbonyl)(P(4-CH₃O-C₅H₄)3)2rhodium(I) 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 803-17-8 Tris(4-methoxyphenyl)phosphine oxide 

Downstream Products

• 62779-23-1 (Methoxycarbonylamino-methyl)-tris-(4-methoxy-phenyl)-phosphonium; chloride 
• 62779-12-8 Isocyanatomethyl-tris-(4-methoxy-phenyl)-phosphonium; chloride 
• 24801-29-4 Tris-(4-methoxy-phenyl)-<2,7-dibrom-fluorenyliden-(9)>-phosphoran 
• 15676-95-6 Tris-(4-methoxy-phenyl)-ethoxycarbonyl-methylen-phosphoran-hydrobromid 
• 1486-15-3 Tris-<4'-methoxy-phenyl>-<2,4-dinitro-phenyl>-phosphonium-pikrat 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 102268-46-2 C₂₅H₂₁O₆P 
• 5076-20-0 2,3-dimethyl-2,3-epoxybutane 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 803-17-8 Tris(4-methoxyphenyl)phosphine oxide 
• 73116-90-2 2,2,2-Tris-(4-methoxy-phenyl)-4,4,5,5-tetramethyl-2λ⁵-[1,3,2]dioxaphospholane 
• 67-64-1 acetone 
• 1050-47-1 Methyltris(p-methoxyphenyl)phosphonium iodide 
• 107770-02-5 neopentyl-tris(p-methoxyphenyl)phosphonium iodide 

Relevant articles and documents

Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

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.).

Synthesis method of phosphine (III) compound

The invention aims to provide an aryl phosphine oxide compound as a raw material, wherein P=O keys are activated by an acid anhydride and alkali is continued. The preparation of the phosphine (III) compound is carried out under the action of a crown ether and a reducing agent. The method has the advantages of cheap and easily available raw materials, simple operation, high atomic economy and the like. Compared with a traditional reduction mode, the method is ingenious in design, waste emission is reduced, separation of intermediate products is omitted, and related reagents such as silicon hydrogen, aluminum, boron and the like with higher price can be avoided. And the reaction suitability is extensive.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

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.

Synthesis method of triphenylphosphine derivative tri-(R-phenyl) phosphine

The invention relates to a synthesis method of a triphenylphosphine derivative tri-(R-phenyl) phosphine. The synthesis method comprises the following steps: adding magnesium chips, a solvent and R-substituted halobenzene into a reaction kettle under the protection of nitrogen, initiating a reaction at a proper temperature, and dropwise adding an R-substituted halobenzene solution to synthesize anintermediate; dropwise adding a phosphorus trichloride solution to complete a Grignard reaction; dropwise adding diluted hydrochloric acid for hydrolysis after negative-pressure desolvation; and carrying out post-treatment to obtain TRPP. According to the method, the tri-(R-phenyl) phosphine of which the purity is greater than 99% is obtained with high selectivity and high yield.

Organic long afterglow material with photoactivation characteristic as well as preparation method and application thereof

The invention discloses an organic long afterglow material with photoactivation characteristic, and a preparation method and application thereof. The chemical structure of the material has a general formula; and R in the formula is H, F, OCH3. According to the invention, the series of compounds are prepared by taking a triphenylphosphine oxide derivative as a research object and connecting different substituents to three benzene ring para-positions of triphenylphosphine oxide. after controlling of the ultraviolet irradiation time, the phosphorescence service life and the intensity of the series of materials are obviously improved. And in combination with different dynamic adjustability, multiple information encryption applications are realized.

Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst

The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.

Mild Reduction of Phosphine Oxides with Phosphites To Access Phosphines

A new method for the iodine-catalyzed reduction of phosphine oxides with phosphites at room temperature is reported. The mild reaction conditions, scalability, and simple purification requirements render it a method of choice for the large-scale production and facile regeneration of a variety of phosphines. Mechanistic studies, supported by DFT calculations of the oxygen transfer between the starting phosphine oxide and the phosphite reagent, are also presented. Such transmutations of phosphorus species were previously unknown.