Tris(2-methylphenyl)phosphin
P(o-tol)3 · TRI-O-TOLYLPHOSPHINE · P(o-tolyl)3 · Tri-o-tolylphosphane · TRIS(2-METHYLPHENYL)PHOSPHINE · TRIS(O-TOLYL)PHOSPHINE · TRI-O-TOLYPHOSPHINE · tris(2-Methylphenyl)phosphane
Identifikatoren & physikalische Daten
| CAS No. | 6163-58-2 |
|---|---|
| Summenformel | C21H21P |
| Durchschnittliche Molmasse | 304,4 g/mol |
| Monoisotopische Masse | 304,1380873 g/mol |
| SMILES | Cc1ccccc1P(c1ccccc1C)c1ccccc1C |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| PubChem CID | 80271 |
| EC No. | 228-193-9 |
| DTXSID | DTXSID9064130 |
| Lokaler Name | Tris(2-methylphenyl)phosphin |
Chemische & physikalische Eigenschaften
| XLogP | 5,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 286 |
| Stoffklassen | Other Classes -> Phosphorus Compounds |
| SpringerMaterials Properties | Crystal structure |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 123-125 °C(lit.) |
| Siedepunkt | 412.4±44.0 °C(Predicted) |
| Dichte | 1.16[at 20℃] |
| Dampfdruck | 0Pa at 20℃ |
| Flammpunkt | 198°C (388°F) |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Chloroform, Ethyl AcetateSoluble in alcohol. Slightly soluble in cold water. Insoluble in water. |
| Aggregatzustand | Crystalline Powder |
| Farbe | White |
| BRN | 661212 |
| InChI | 1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3 |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| SMILES | Cc1ccccc1P(c2ccccc2C)c3ccccc3C |
| LogP (Verteilungskoeffizient) | 7.2 |
| CAS Datenbank | 6163-58-2(CAS DataBase Reference) |
| NIST chemische Informationen | Phosphine, tris(2-methylphenyl)-(6163-58-2) |
| EPA chemische Informationen | Phosphine, tris(2-methylphenyl)- (6163-58-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.9% (1 of 113) of reports.WarningH315 (89.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 113 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 10-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24651Tri(o-tolyl)-phosphine: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin and strong eye irritant[Sigma-Aldrich MSDS] See Triphenylphosphine. |
| Hazard Classes and Categories | Skin Irrit. 2 (89.4%) |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29319090 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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 %)