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| | Tri(o-tolyl)phosphine Basic information |
| | 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℃ | | Fp | 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) |
| | Tri(o-tolyl)phosphine Usage And Synthesis |
| 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 %) | | Flammability and Explosibility | Notclassified | | Purification Methods | It crystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 III 835.] |
| | Tri(o-tolyl)phosphine Preparation Products And Raw materials |
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