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: 41

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

Chemical Properties

White to pale yellow crystalline powder

Uses

suzuki reaction

Uses

Tris(4-methoxyphenyl)phosphine is a useful intermediate employed in organic synthesis and in other chemical processes.

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

• 855388-71-5 Phenethylamine, p-ethyl--bta--methyl- (5CI) 
• 855386-66-2 8-Oxabicyclo[5.1.0]octane, 4-methyl- 
• 855386-64-0 8-oxa-bicyclo[3.2.1]octane-3-carbonitrile 
• 85538-51-8 1-(tricyclo[4.3.1.1~2,5~]undec-10-yl)pyrrolidine 
• 85538-50-7 10-methoxytricyclo[4.3.1.1~2,5~]undecane 
• 855384-62-2 1,1-Cyclobutanedicarboxamide, 3-methyl- 
• 85538-41-6 S-butan-2-yl O-ethyl ethyl(thioformyl)phosphoramidodithioate 
• 855383-99-2 INDEX NAME NOT YET ASSIGNED 
• 855383-80-1 7-Oxabicyclo[4.1.0]heptane, 1-chloro-6-methyl- 
• 855383-79-8 7-Oxabicyclo[4.1.0]heptane, 1-ethyl-3-methyl- 
• 855383-78-7 7-Oxabicyclo[4.1.0]heptane, 1-methoxy-3-methyl- 
• 855383-75-4 7-Oxabicyclo[4.1.0]heptane, 1,3,3-trimethyl- 
• 855383-57-2 6-Oxa-3-azabicyclo[3.1.0]hexane, 1,5-dimethyl- 
• 855383-29-8 N-benzyl-2-(4-methoxyphenyl)-1-ethanamine hydrochloride 

Downstream Products

• 855389-47-8 5-Propyl-1,3,4-oxadiazol-2-ol 
• 855389-68-3 Oxalacetic acid, chloro(hydroxymethyl)-, -gamma--lactone (5CI) 
• 855391-76-3 Phenethylamine, -bta-,2,4-trimethyl- (5CI) 
• 85539-30-6 2-[[2-(Acetyloxy)benzoyl]oxy]benzoic Acid 2-[(2-Carboxyphenoxy)carbonyl]phenyl Ester 
• 85539-36-2 3-[2-(5-Cyano-1,2-dihydro-6-hydroxy-4-Methyl-2-oxo-3-pyridinyl)diazenyl]-4-Methoxybenzenesulfonic Acid 
• 85539-83-9 P-XSC 
• 85539-84-0 ETHYL BROMOACETATE-2-13C 
• 855398-51-5 1-Oxaspiro[2.5]octane, 2,4-dimethyl- 
• 855398-57-1 6-oxaspiro [4.5] decan-9-one 
• 855398-58-2 6-Oxaspiro[4.5]decan-9-ol 
• 855399-88-1 2,4,6-Cycloheptatrien-1-one, 3-amino-2-hydroxy-4-methyl- 
• 855400-66-7 3-Bromo-5-methoxyphenol 
• 855400-82-7 5-BroMo-4-chloro-2-nitrophenol 
• 855402-67-4 2,4,6-Cycloheptatrien-1-one, 2-chloro-7-mercapto- 

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