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 

Yes

HS Code 

29310095

MSDS

• Language:English Provider:Bis(1,2-diphenylphosphino)ethane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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(1663-45-2)Related Product Information

• Hexafluoroethane
• ETHANE
• 3,4'-DIAMINODIPHENYLMETHANE
• 1,5-Diphenylcarbazide
• N-(Carboxymethyl)-N-(phosphonomethyl)-glycine
• 4,4'-DDT
• Chlorodiphenylphosphine
• 1,1'-Bis(diphenylphosphino)ferrocene
• 1,3-Bis(diphenylphosphino)propane
• Bis(diphenylphosphino)methane
• [1,2-Bis(diphenyphosphino)ethane]dichlorocobalt(II)
• 1,2,3,4-DIEPOXYBUTANE
• [1,2-Bis(diphenyphosphino)ethane]dichloroiron(II)
• R-(+)-1,2-BIS(DIPHENYLPHOSPHINO)PROPANE
• (2R,3R)-(+)-BIS(DIPHENYLPHOSPHINO)BUTANE
• (2S,3S)-(-)-BIS(DIPHENYLPHOSPHINO)BUTANE
• ETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)
• (2R,3R)-(-)-2,3-BIS(DIPHENYLPHOSPHINO)BICYCLO[2.2.1]HEPT-5-ENE