Diphenyl-2-pyridylphosphine CAS 37943-90-1
Diphenyl-2-pyridylphosphine Basic informationReaction
| Product Name: | Diphenyl-2-pyridylphosphine |
| Synonyms: | 2-Pyridyldiphenylphosphine;Diphenyl(2-pyridinyl)phosphine;2-(diphenylphosphanyl)pyridine;2-Diphenylphosphinopyridine, min. 97%;DPPPY/DIPHENYL-2-PYRIDYL;Diphenyl-2-pyridylphosphine 97%;DIPHENYL-2-PYRIDYLPHOSPHINE;2-(DIPHENYLPHOSPHINO)PYRIDINE |
| CAS: | 37943-90-1 |
| MF: | C17H14NP |
| MW: | 263.27 |
| EINECS: | 629-049-1 |
| Product Categories: | Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chelating Agents & Ligands;Phosphines;Mitsunobu Reaction;Phosphine Ligands;Phosphines (Mitsunobu Reaction);Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;Achiral Phosphine;Aryl Phosphine |
| Mol File: | 37943-90-1.mol |
Diphenyl-2-pyridylphosphine Chemical Properties
| Melting point | 82-84 °C (dec.) (lit.) |
| Boiling point | 163 °C(Press: 0.05 Torr) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Soluble in toluene. (almost transparency) |
| pka | 2.37±0.12(Predicted) |
| form | Crystalline Powder |
| color | White to yellow to tan |
| InChI | InChI=1S/C17H14NP/c1-3-9-15(10-4-1)19(16-11-5-2-6-12-16)17-13-7-8-14-18-17/h1-14H |
| InChIKey | SVABQOITNJTVNJ-UHFFFAOYSA-N |
| SMILES | C1(P(C2=CC=CC=C2)C2=CC=CC=C2)=NC=CC=C1 |
| CAS DataBase Reference | 37943-90-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Chronic 4 Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Reaction | Ligand for the palladium-catalyzed distannylation of ortho-quinodimethanes Ligand for the palladium-catalyzed disilylation of o-quinodimethanes to synthesize 9- and 10-membered disilacarbocycles Ligand for the palladium-catalyzed alkoxycarbonylation of allenes |
| Chemical Properties | Yellow to orange crystalline powder |
| Uses | Diphenyl-2-pyridylphosphine is an organophosphorous compound that is a widely used mono-pyridylphosphine ligand in transition metal complexes for catalysis. |
| Uses | suzuki reaction |
| Uses | Ligand for metal-catalyzed carbonylations, hydration, dehydrogenative coupling, carbostannylation, distannylation, and silylation; reagent for Mitsunobu reaction. |
| Application | Diphenyl-2-pyridylphosphine is a functionally diverse and important fine chemical. Its core value lies in its participation in catalytic reactions as an efficient ligand, thus playing a key role in drug synthesis, new materials development, and the chemical industry. |
| reaction suitability | reagent type: ligand reaction type: Carbonatations reagent type: ligand reaction type: Dehydrogenation reagent type: ligand reaction type: Hydration Reaction reagent type: ligand reaction type: Mitsunobu Reaction reagent type: ligand reaction type: Stannylation |
| Synthesis | 5029-67-4 829-85-6 37943-90-1 General procedure for the synthesis of diphenyl-2-pyridylphosphine from 2-iodopyridine and diphenylphosphine: MCM-41-3N-Pd(0) (21 mg, 0.01 mmol), KOAc (1.5 mmol), and 2-iodopyridine (1.0 mmol, if solid) were placed in an oven-dried 20 mL Schlenk tube. The vessel was evacuated and displaced three times with argon. Subsequently, 2-iodopyridine (1.0 mmol, if liquid), diphenylphosphine (1.2 mmol) and DMAc (1 mL) were added by syringe under argon protection. The reaction mixture was stirred at 130 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, diluted with CH2Cl2 (20 mL) and filtered.The MCM-41-3N-Pd(0) catalyst was washed with distilled water (2 × 5 mL) and ethanol (2 × 5 mL) for next use. The filtrate was concentrated under vacuum and the residue was purified by fast column chromatography on silica gel to obtain the target product diphenyl-2-pyridylphosphine. |
| References | [1] Journal of Organometallic Chemistry, 2018, vol. 866, p. 50 - 58 [2] Applied Organometallic Chemistry, 2018, vol. 32, # 8, |
Diphenyl-2-pyridylphosphine Preparation Products And Raw materials
| Raw materials | Ethanol-->Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Sodium-->PETROLEUM ETHER-->Magnesium sulfate-->Acetone-->n-Butyllithium-->Ammonium chloride-->Triphenylphosphine-->Lithium-->2-Chloropyridine-->Diphenylphosphine-->Pyridine, 2-(diphenylphosphinyl)--->Diphenyl(trimethylsilyl)phosphine |
