1,2-Bis(diphenylphosphino)ethane CAS 1663-45-2
Introduction：Basic information about 1,2-Bis(diphenylphosphino)ethane CAS 1663-45-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1,2-Bis(diphenylphosphino)ethane Basic information
| Product Name: | 1,2-Bis(diphenylphosphino)ethane |
| Synonyms: | 1,2-Bis(diphenylphos;1,2-Bis(diphenylphosphino)ethane, 98+% 10GR;1,2-Bis(diphenylphosphino)ethane, 98+% 50GR;98% DPPE;Ethylenebis(diphenylphosphine)DPPE;1,2-Bis(diphenylphosphono)ethane;1,2-Bis(diphenylphosphiNA)ethane;1,2-Bis(diphenylphosphino)etha |
| CAS: | 1663-45-2 |
| MF: | C26H24P2 |
| MW: | 398.42 |
| EINECS: | 216-769-2 |
| Product Categories: | Ligand;Phosphines;Phosphine Ligands;Synthetic Organic Chemistry;organophosphine ligand;Achiral Phosphine;Aryl Phosphine |
| Mol File: | 1663-45-2.mol |
1,2-Bis(diphenylphosphino)ethane Chemical Properties
| Melting point | 137-142 °C (lit.) |
| Boiling point | 514.8±33.0 °C(Predicted) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Soluble in acetone, methanol and alcoholic hydrochloric acid. |
| form | Crystalline Powder or Crystals |
| color | White to off-white |
| Sensitive | Air Sensitive |
| BRN | 761261 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. May be air-sensitive. |
| InChI | InChI=1S/C26H24P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20H,21-22H2 |
| InChIKey | QFMZQPDHXULLKC-UHFFFAOYSA-N |
| SMILES | C1C=CC=CC=1P(CCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 |
| CAS DataBase Reference | 1663-45-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Phosphine, 1,2-ethanediylbis[diphenyl-(1663-45-2) |
| EPA Substance Registry System | Phosphine, 1,2-ethanediylbis[diphenyl- (1663-45-2) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-37/39-26-36 |
| WGK Germany | 3 |
| F | 9 |
| TSCA | TSCA listed |
| HS Code | 29310095 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | STOT SE 3 |
| Chemical Properties | white to light yellow crystal powde |
| Uses | suzuki reaction |
| Uses | 1,2-Bis(diphenylphosphino)ethane is a bidendate ligand used in coordination chemistry to prepare metal complexes. It is involved in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. It is also used in 1,3-diene synthesis. Further, it is used in cycloaddition reactions and carbonylation reactions. In addition to this, it is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation. |
| Definition | ChEBI: 1,2-bis(diphenylphosphino)ethane is a tertiary phosphine and a member of diphosphanes. It has a role as an allergen. |
| reaction suitability | reagent type: ligand reaction type: C-C Bond Formation reagent type: ligand reaction type: Carbonylations reagent type: ligand reaction type: Cycloadditions reagent type: ligand reaction type: Decarboxylations reagent type: ligand reaction type: Diels-Alder Reaction reagent type: ligand reaction type: Heck Reaction reagent type: ligand reaction type: Negishi Coupling reagent type: ligand reaction type: Suzuki-Miyaura Coupling |
| Mechanism of action | 1,2-Bis(diphenylphosphino)ethane (DPPE) and its synthetic analogues are important structural motifs in organic synthesis, particularly as diphosphine ligands with a C2-alkyl-linker chain. Since DPPE is known to bind to many metal centers in a bidentate fashion to stabilize the corresponding metal complex via the chelation effect originating from its entropic advantage over monodentate ligands, it is often used in transition-metal-catalyzed transformations. |
| Synthesis | Several synthetic methods to produce 1,2-Bis(diphenylphosphino)ethane (DPPE) exist; however, most of these methods are limited to substitution reactions of highly reactive alkali metal diphenylphosphides (e.g., Ph2PM; M = Li or Cs) with 1,2-dihaloethanes (X−CH2−CH2−X; X = Cl, Br, and I) in an SN2 fashion (Eq. 1). Moreover, there are a few methods using the alkoxide-base (KOt-Bu)-catalyzed hydrophosphination of vinyl phosphines (Eq. 2) with diphenylphosphines9 or the dihydrophosphination of acetylene gas (Eq. 3). [1] |
| Purification Methods | Recrystallise it from aqueous EtOH or *C6H6. The dimethiodide, when recrystallised from MeOH has m 305-307o, and the dioxide when recrystallised from toluene or DMF (needles), or *C6H6 (plates) has m 252-254o (276-278o) [Isslieb et al. Chem Ber 92 3175 1959, NMR: Aquiar et al. J Org Chem 29 1660 1964, B.ckvall et al. J Org Chem 52 5430 1987]. [Beilstein 16 IV 958.] |
| References | [1] Takano, H., Katsuyama, H., Hayashi, H. et al. A theory-driven synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane analogues via radical difunctionalization of ethylene. Nat Commun 13, 7034 (2022). |
1,2-Bis(diphenylphosphino)ethane Preparation Products And Raw materials
| Raw materials | Ethanol-->Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Sodium-->PETROLEUM ETHER-->Magnesium sulfate-->Acetone-->n-Butyllithium-->Triphenylphosphine-->1,2-Dichloroethane-->Lithium-->1,2-Dibromoethane-->Diphenylphosphine |
| Preparation Products | 1.1'-Binaphthyl-2.2'-diphemyl phosphine-->(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->Bis(diphenylphosphino)methane-->TETRACHLOROCATECHOL-->Dichloro(DPPE)digold(I) ,96% |
