TRI-P-TOLYLPHOSPHINE Chemical Properties

Melting point:

144-148 °C(lit.)

Boiling point:

399.8±41.0 °C(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystals or Crystalline Powder

color 

White to light yellow

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

651045

InChI

InChI=1S/C21H21P/c1-16-4-10-19(11-5-16)22(20-12-6-17(2)7-13-20)21-14-8-18(3)9-15-21/h4-15H,1-3H3

InChIKey

WXAZIUYTQHYBFW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1038-95-5(CAS DataBase Reference)

EPA Substance Registry System

Phosphine, tris(4-methylphenyl)- (1038-95-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

SZ3880000

F 

10-23

TSCA 

Yes

HS Code 

29319090

MSDS

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

TRI-P-TOLYLPHOSPHINE Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

suzuki reaction

Uses

Tri(p-tolyl)phosphine is used as pharmaceutical intermediate.

Application

Tri-p-tolylphosphine is commonly used in pharmaceutical manufacturing as a ligand in catalysis, particularly in palladium-catalyzed cross-coupling reactions. These reactions are crucial for forming carbon-carbon bonds in drug synthesis.

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

20 g Sodium (0.870 mol) was added to 125 ml toluene, then the mixture was heated up to 383 K and stirred to form fine particles of sodium, which subsequently melted. Then the temperature was lowered to 323 K. P-chlorotoluene (55.2 g /0.436 mol) and phosphorus trichloride (19.8 g / 0.144 mol) were added, keeping the temperature between 323 K and 333 K for two hours. The product was concentrated in a vacuum to gain a white solid (35.0 g, 80%) (Brown et al., 1988). The pure title compound (TRI-P-TOLYLPHOSPHINE) was obtained by crystallizing from methanol.[1]

References

[1] Tri-p-tolyl­phosphine. Crystallographic Communications. August 2008 64(Pt 9):o1783-o1783

TRI-P-TOLYLPHOSPHINE(1038-95-5)Related Product Information

• Tributyl(2-phenylethenyl)stannane
• DICHLOROTRIS(TRIPHENYLPHOSPHINE)RUTHENIUM(II)
• METHYLTRIBUTYLPHOSPHONIUM IODIDE
• Tributylphosphine
• TRI-N-BUTYLPHOSPHINE OXIDE
• TRIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]PHOSPHINE
• Triphenylphosphine
• TRIS(PENTAFLUOROPHENYL)BORANE
• TRIS(PENTAFLUOROPHENYL)PHOSPHINE
• Tris(nonylphenyl) phosphite
• TRIS(2-METHOXYPHENYL)PHOSPHINE
• PHOSPHOROUS ACID TRIS(4-METHYLPHENYL) ESTER
• TRIMESITYLPHOSPHINE
• TRI-P-TOLYLPHOSPHINE
• TRIS[4-(PERFLUOROOCTYL)PHENYL]PHOSPHINE
• TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE
• Dibromobis(tri-o-tolylphosphine)palladium(II), Pd 12%
• Tri(o-tolyl)phosphine