Tris(4-methoxyphenyl)phosphine Chemical Properties

Melting point:

131-134 °C (lit.)

Boiling point:

457.8±40.0 °C(Predicted)

Density 

1.1352 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystalline Powder

color 

White to pale yellow

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

2815911

InChI

InChI=1S/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

InChIKey

UYUUAUOYLFIRJG-UHFFFAOYSA-N

SMILES

P(C1=CC=C(OC)C=C1)(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1

CAS DataBase Reference

855-38-9(CAS DataBase Reference)

EPA Substance Registry System

Phosphine, tris(4-methoxyphenyl)- (855-38-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Tris(4-methoxyphenyl)phosphine Usage And Synthesis

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.

Application

Tris(4-methoxyphenyl)phosphine is used as a ligand in organometallic chemistry and homogeneous catalysis.
This compound is suitable for the following reaction types: Buchwald-Hartwig Cross Coupling Reaction, Heck Reaction, Hiyama Coupling, Negishi Coupling, Sonogashira Coupling, Stille Coupling, Suzuki-Miyaura Coupling, and Cross Couplings.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

Synthesis

To a solution of tertiary phosphine oxides 2 (0.4mmol) in CH2Cl2 (2mL) was added oxalyl chloride (0.4mmol) dropwise at room temperature under an argon atmosphere. After 30 minutes, HEH (1mmol) was added to the mixture in one portion, and TEA (3mmol) was added. The mixture was stirred for another 2h at 40°C and then diluted with H2O (10mL). The resulting mixture was extracted with CH2Cl2 repeatedly. The extracts were dried (anhydrous Na2SO4) and evaporated. The crude product was purified by column chromatography on silica gel using ethyl acetate/petroleum ether to afford the pure product Tris(4-methoxyphenyl)phosphine.

References

[1] Synthesis, 2011, # 24, p. 4091 - 4098
[2] Tetrahedron Letters, 2015, vol. 56, # 7, p. 918 - 920
[3] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 176 - 178
[4] ChemCatChem, 2017, vol. 9, # 24, p. 4460 - 4464
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 50, p. 15989 - 15992

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