2-(Dicyclohexylphosphino)biphenyl CAS 247940-06-3
Introduction：Basic information about 2-(Dicyclohexylphosphino)biphenyl CAS 247940-06-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-(Dicyclohexylphosphino)biphenyl Basic informationReaction
| Product Name: | 2-(Dicyclohexylphosphino)biphenyl |
| Synonyms: | CYCLOHEXYL JOHNPHOS;2-(DICYLOHEXYLPHOSPHINO)BIPHENYL;2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL;(2-BIPHENYLYL)DICYCLOHEXYLPHOSPHINE;2-(Dicyclohexylphosphino)biphenyl2-(Dicyclohexylphosphino)biphenyl;2-(Dicyclohexylphosphino)biphenyl,98%;(2-biphenyl)dicyclohexylphosphine;2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL 98% |
| CAS: | 247940-06-3 |
| MF: | C24H31P |
| MW: | 350.48 |
| EINECS: | 480-030-2 |
| Product Categories: | Phosphine Ligands;Synthetic Organic Chemistry;organophosphine ligand;Ligand;Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Buchwald Ligands&Precatalysts;Phosphines |
| Mol File: | 247940-06-3.mol |
2-(Dicyclohexylphosphino)biphenyl Chemical Properties
| Melting point | 102-106 °C(lit.) |
| Boiling point | 499.5±24.0 °C(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | soluble in Toluene |
| form | crystal |
| color | white |
| Sensitive | Air Sensitive |
| BRN | 8440533 |
| InChI | InChI=1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2 |
| InChIKey | LCSNDSFWVKMJCT-UHFFFAOYSA-N |
| SMILES | P(C1=CC=CC=C1C1=CC=CC=C1)(C1CCCCC1)C1CCCCC1 |
| CAS DataBase Reference | 247940-06-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 36/37/38-22 |
| Safety Statements | 36/37/39-26 |
| WGK Germany | 3 |
| F | 10-13-23 |
| TSCA | No |
| HazardClass | AIR SENSITIVE |
| HS Code | 29310099 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Chronic 4 |
| Reaction |
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| Description | 2-(Dicyclohexylphosphino)biphenyl is a ligand for the amination of triflates and aryl halides. Optimal ligand for a novel amination reaction (Buchwald reaction)(2) 2-(Dicyclohexylphosphino)biphenyl, a synthetic chemical compound, has found diverse applications in scientific research. Being a cyclic phosphonate derivative of cyclohexanol, this colourless, odourless, and tasteless solid holds a distinct appeal for laboratory use. In scientific research, 2-(Dicyclohexylphosphino)biphenyl has proven invaluable. It serves as an excellent model compound for delving into protein-ligand interactions, thus aiding in studying small molecule effects on protein folding. Moreover, researchers have utilized 2-(Dicyclohexylphosphino)biphenyl to gain insights into protein structures and unravel the mechanism of action behind various drugs. Additionally, the compound has been a vital tool in assessing how environmental factors influence protein structure and function. The interaction between 2-(Dicyclohexylphosphino)biphenyl and proteins primarily occurs through hydrogen bonding and hydrophobic interactions, resulting in high-affinity and specific protein binding. |
| Chemical Properties | white to light yellow crystal powde |
| Uses | Ligand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates. |
| Uses | suzuki reaction |
| Uses | 2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions. |
| General Description | CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. |
| reaction suitability | reaction type: Cross Couplings reagent type: ligand reaction type: Arylations reagent type: ligand reaction type: Buchwald-Hartwig Cross Coupling Reaction reagent type: ligand reaction type: C-X Bond Formation reagent type: ligand reaction type: Hiyama Coupling reagent type: ligand reaction type: Methylations reagent type: ligand reaction type: Negishi Coupling reagent type: ligand reaction type: Oxidations reagent type: ligand reaction type: Suzuki-Miyaura Coupling |
| Synthesis | 2052-07-5 829-84-5 247940-06-3 General procedure for the synthesis of 2-(dicyclohexylphosphino)biphenyl from 2-bromobiphenyl and dicyclohexylphosphine: under nitrogen protection, a mixture of L1 (0.05 or 0.10 mmol P), [PdCl(η3-C3H5)]2 (0.025 mmol), 2-bromobiphenyl (0.55 mmol) and dicyclohexylphosphine (0.50 mmol) was reacted in a 20 M KOH The mixture in aqueous solution (0.5-1.0 mL) was reacted by shaking at 100 °C for several hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The aqueous filtrate was extracted with degassed toluene (2 mL x 2 times). For the recovered catalyst resin beads, extract with degassed toluene (2 mL x 4 times). All extracts were combined and dried with anhydrous Na2SO4, followed by concentration under vacuum to obtain the crude product. The crude product was purified by silica gel fast chromatography using degassed eluent (n-hexane/Et2O = 10/0-9/1), and the purification process was completed by a YAMAZEN medium-pressure liquid chromatography system, which ultimately yielded the target product 2-(dicyclohexylphosphino)biphenyl. |
| References | [1] Synlett, 2017, vol. 28, # 20, p. 2966 - 2970 |
2-(Dicyclohexylphosphino)biphenyl Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->n-Butyllithium-->Magnesium-->Phosphorus trichloride-->Copper(I) chloride-->Diethylamine-->Cyclohexane-->Bromobenzene-->Nickel(II) chloride hexahydrate-->Cinchonidine-->Bromocyclohexane-->1,2-Dibromobenzene-->2-Bromobiphenyl-->Methanesulfonic acid, 1,1,1-trifluoro-, [1,1'-biphenyl]-2-yl ester-->Dicyclohexylphosphine-->Dicyclohexylchlorophosphine |
