Tri(o-tolyl)phosphine Chemical Properties

Melting point:

123-125 °C(lit.)

Boiling point:

412.4±44.0 °C(Predicted)

Density 

1.16[at 20℃]

vapor pressure 

0Pa at 20℃

Flash point:

198°C (388°F)

storage temp. 

Store below +30°C.

solubility 

Chloroform, Ethyl Acetate

form 

Crystalline Powder

color 

White

Water Solubility 

Soluble in alcohol. Slightly soluble in cold water. Insoluble in water.

Sensitive 

air sensitive

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

BRN 

661212

InChIKey

COIOYMYWGDAQPM-UHFFFAOYSA-N

LogP

7.2

CAS DataBase Reference

6163-58-2(CAS DataBase Reference)

NIST Chemistry Reference

Phosphine, tris(2-methylphenyl)-(6163-58-2)

EPA Substance Registry System

Phosphine, tris(2-methylphenyl)- (6163-58-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-23

TSCA 

Yes

HS Code 

29319090

MSDS

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

Tri(o-tolyl)phosphine Usage And Synthesis

Description

Tris(o-tolyl)phosphine is an organophosphorus compound. This compound is a white, water-insoluble solid that is soluble in organic solvents. In solution, it slowly converts to the phosphine oxide. As a phosphine ligand, it has a wide cone angle of 194°. Consequently, it tends to cyclometalate when treated with metal halides and metal acetates. Complexes of this ligand are common in homogeneous catalysis.

Chemical Properties

white to light yellow crystal powder.

Uses

Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.

Application

Tris(2-methylphenyl)phosphine (Eletriptan Impurity 13) is a phosphine catalyst. It can be used in the rhodium-catalyzed hydrogenation, Suzuki-Miyaura cross-coupling reactions and Heck reactions.

Preparation

Tri(o-tolyl)phosphine can be obtained by the reduction of tris(o-tolyl)phosphine oxide or prepared by the 2-bromotoluene Grignard reaction.
Procedure: To a solution of magnesuim turnings (3.11 g, 128 mmol, 3.5 equiv) in THF (50 mL) was added a small amount of 2-bromotoluene (1 mL) and 1 iodine crystal. The reaction vessel was heated until initiation occurred, where upon a solution of the remaining 2-bromotoluene (20 g, 117 mmol, 3.2 equiv in total) in THF (100 mL) was added. The reaction was set to reflux for 2 hours (colour change to black solution), after which it was cooled to 0 oC and a solution of phosphorus trichloride (5.01 g, 36.5 mmol, 1 equiv) in THF (30 mL) was added dropwise. Upon addition completion the reaction was set to reflux for 18 hours. The reaction was allowed to cool to room temperature, whereupon NH4Cl solution was added with care. The resulting solution was extracted with ether (3 x 100 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalised from ethanol to yield Tri(o-tolyl)phosphine as a white solid. (6.8 g, 62 %)

Reactivity Profile

Tri(o-tolyl)phosphine is suitable for the following reaction types: Cross Couplings, Silylations, Buchwald-Hartwig Cross Coupling Reaction, Heck Reaction, Negishi Coupling, Stille Coupling, Suzuki-Miyaura Coupling.

Flammability and Explosibility

Not classified

Purification Methods

It crystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 III 835.]

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