| Identification | More | [Name]
1,2-Bis(diphenylphosphino)ethane | [CAS]
1663-45-2 | [Synonyms]
1,2-BIS(DIPHENYLPHOSPHINE)ETHANE
1,2-BIS(DIPHENYLPHOSPHINO)ETHANE
BIS(1,2-DIPHENYLPHOSPHINO)ETHANE
BIS(DIPHENYLPHOSPHINO)ETHANE
DIPHOS
DPPE
ETHYLENEBIS(DIPHENYLPHOSPHINE)
[2-(Diphenylphosphino)ethyl](diphenyl)phosphine
1,2-Ethanediylbis(diphenylphosphine)
1,2-ethanediylbis[diphenyl-phosphin
bis(diphenylphosphine)ethane
P,P'-Ethylenebis(diphenylphosphine)
Phosphine, 1,2-ethanediylbis*diphenyl-
Phosphine, ethylenebis*diphenyl-
Phosphine, ethylenebis[diphenyl-
1,2-Bis(Diphenylphosphor) Ethane
1,2-Bis(diphenylphosphino)ethane(dppe)
1,2-Bis(diphenylphosphino)ethane, 98+%
1,2-bis(diphenyphosphino)ethane
1,2-Bis(diphenylphosphino)ethane,99%DIPHOS | [EINECS(EC#)]
216-769-2 | [Molecular Formula]
C26H24P2 | [MDL Number]
MFCD00003047 | [Molecular Weight]
398.42 | [MOL File]
1663-45-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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 | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. May be air-sensitive. | [Sensitive ]
Air Sensitive | [Detection Methods]
HPLC,NMR | [BRN ]
761261 | [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) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
1663-45-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H335 | [Precautionary statements ]
P261-P271-P304+P340+P312-P403+P233-P405-P501 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
9 | [TSCA ]
Yes | [HS Code ]
29310095 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
suzuki reaction | [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). |
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