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
• Article Data: 27

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

Description

TRIS(4-METHOXYPHENYL)PHOSPHINE is an organic compound that serves as a versatile intermediate in various chemical reactions and processes, including the Suzuki reaction. It is characterized by its phosphine functionality and three 4-methoxyphenyl groups attached to the central phosphorus atom, which contribute to its unique reactivity and properties.

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) 
• 803-17-8 Tris(4-methoxyphenyl)phosphine oxide 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 

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 
• 803-17-8 Tris(4-methoxyphenyl)phosphine oxide 
• 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 
• 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.

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.