Tri(o-tolyl)phosphine
- CAS No.
- 6163-58-2
- Chemical Name:
- Tri(o-tolyl)phosphine
- Synonyms
- P(o-tol)3;TRI-O-TOLYLPHOSPHINE;Tri-o-tolylphosphane;TRIS(2-METHYLPHENYL)PHOSPHINE;TRI-O-TOLYPHOSPHINE;TRIS(O-TOLYL)PHOSPHINE;tris(2-Methylphenyl)phosphane;tri-o-tolyl phopine;Tri-ortho-tolylphosphine;TRI(2-METHYLPHENYL)PHOSPHINE
- CBNumber:
- CB8128012
- Molecular Formula:
- C21H21P
- Molecular Weight:
- 304.37
- MOL File:
- 6163-58-2.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/3/8 15:11:15
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
Tri(o-tolyl)phosphine price More Price(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 8.41817 | Tri(o-tolyl)-phosphine for synthesis | 6163-58-2 | 1G | ₹3380 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.41817 | Tri(o-tolyl)-phosphine for synthesis | 6163-58-2 | 10G | ₹9620 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 287822 | Tri(o-tolyl)phosphine 97% | 6163-58-2 | 1G | ₹2700 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 287822 | Tri(o-tolyl)phosphine 97% | 6163-58-2 | 10G | ₹10020 | 2022-06-14 | Buy |
| ALFA India | ALF-A12093-14 | Tri(o-tolyl)phosphine, 98+% | 6163-58-2 | 25g | ₹16855 | 2022-05-26 | Buy |
Tri(o-tolyl)phosphine Chemical Properties,Uses,Production
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.
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
Raw materials
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|---|---|---|---|---|---|
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| Supplier | Advantage |
|---|---|
| GLR Innovations | 58 |
| NSR Laboratories Pvt. Ltd. | 58 |
| VASISTA LIFE SCIENCES PRIVATE LIMITED | 58 |
| SPD CHEMICALS | 58 |
| AMINO ORGANICS | 58 |
| Shiv pharma chem | 58 |
| JSK Chemicals | 58 |
| Tosco Pharmachem Pvt Ltd | 58 |
| S S Arofine | 58 |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | 58 |
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