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| | 1,2-Bis(diphenylphosphino)ethane Basic information |
| | 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) |
| 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 |
| | 1,2-Bis(diphenylphosphino)ethane Usage And Synthesis |
| 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 |
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