Tri-o-tolylphosphine
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
Identifiers & Physical Properties
| CAS No. | 6163-58-2 |
|---|---|
| Molecular formula | C21H21P |
| Average molar mass | 304.4 g/mol |
| Monoisotopic mass | 304.1380873 g/mol |
| SMILES | Cc1ccccc1P(c1ccccc1C)c1ccccc1C |
| InChIKey | COIOYMYWGDAQPM-UHFFFAOYSA-N |
| PubChem CID | 80271 |
| EC No. | 228-193-9 |
| DTXSID | DTXSID9064130 |
Chemical & Physical Properties
| XLogP | 5.7 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 3 |
| Heavy atoms | 22 |
| Formal charge | 0 |
| Complexity | 286 |
| Chemical classes | Other Classes -> Phosphorus Compounds |
| SpringerMaterials Properties | Crystal structure |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| 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 conditions | Store below +30°C. |
| Solubility | Chloroform, Ethyl AcetateSoluble in alcohol. Slightly soluble in cold water. Insoluble in water. |
| Physical state | Crystalline Powder |
| Color | White |
| Sensitivity | air sensitive |
| Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
| 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 (partition coefficient) | 7.2 |
| CAS DataBase Reference | 6163-58-2(CAS DataBase Reference) |
| FDA UNII | 5M32DK8XA8 |
| NIST Chemistry Reference | Phosphine, tris(2-methylphenyl)-(6163-58-2) |
| EPA Substance Registry System | Phosphine, tris(2-methylphenyl)- (6163-58-2) |
| UNSPSC Code | 12352128 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 3 |
| F | 10-23 |
| TSCA inventory status | TSCA listed |
| Customs code | 29319090 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | 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. |
|---|---|
| Regulatory information | 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 |
| Hazards summary | A skin and strong eye irritant[Sigma-Aldrich MSDS] See Triphenylphosphine. |
| Hazard Classes and Categories | Skin Irrit. 2 (89.4%) |
| F | 10-23 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29319090 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
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.
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.
Preparation & Synthesis
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 %)