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106496

Sigma-Aldrich

Ethylenebis(diphenylphosphine)

97%

Synonym(s):

1,2-Bis(diphenylphosphino)ethane, Diphos, dppe

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About This Item

Linear Formula:
(C6H5)2PCH2CH2P(C6H5)2
CAS Number:
1663-45-2
Molecular Weight:
398.42
Beilstein:
761261
EC Number:
216-769-2
MDL number:
MFCD00003047
UNSPSC Code:
12352002
PubChem Substance ID:
24846735
NACRES:
NA.22

Assay

97%

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

mp

137-142 °C (lit.)

functional group

phosphine

SMILES string

C(CP(c1ccccc1)c2ccccc2)P(c3ccccc3)c4ccccc4

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

InChI key

QFMZQPDHXULLKC-UHFFFAOYSA-N

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Related Categories

Application

Ligand for metal-catalyzed allylic alkylation; decarboxylation of allylic esters; 1,3-diene synthesis; cycloaddition reactions; carbonylation reactions.
Used to obtain mixed-metal clusters.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H335

Hazard Classifications

STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bryan E Barton et al.
Journal of the American Chemical Society, 131(20), 6942-6943 (2009-05-06)
The ferrous dithiolato carbonyl Fe(S(2)C(3)H(6))(CO)(2)(dppe) (1) condenses with NiCl(2)(dppe) to give [FeNi(pdt)(mu-Cl)(CO)(dppe)(2)]BF(4) ([2Cl](+)). The corresponding reaction of the ditosylate Ni(OTs)(2)(dppe) gave the dication [(CO)(2)(dppe)Fe(pdt)Ni(dppe)](OTs)(2) ([2(CO)](OTs)(2)) (pdt = 1,3-propanedithiolate; dppe = 1,2-C(2)H(4)(PPh(2))(2); OTs(-) = CH(3)C(6)H(4)-4-SO(3)(-)). Reduction of the bimetallic dicarbonyl with
William D Kerber et al.
Dalton transactions (Cambridge, England : 2003), (11)(11), 1948-1951 (2005-05-24)
Reaction of (dppe)MCl(2)(dppe = 1,2-bis(diphenylphosphino)ethane) with 2-(N-phenyliminomethyl)phenol leads to air-stable (dppe)M(N,O) chelates (M = Pd, 1a; M = Pt, 1b). The N-4-methylphenyl derivative of 1a has been characterized by X-ray analysis. The N,O ligands are kinetically labile and exchange occurs
Noémie Elgrishi et al.
Journal of the American Chemical Society, 139(1), 239-244 (2016-12-21)
The need for benchmarking hydrogen evolution catalysts has increasingly been recognized. The influence of acid choice on activity is often reduced to the overpotential for catalysis. Through the study of a stable cobalt hydride complex, we demonstrate the influence of
R M Snyder et al.
Cancer research, 46(10), 5054-5060 (1986-10-01)
Bis(diphenylphosphine)ethane (DPPE) and its bis[chlorogold(I)] [DPPE(Au2Cl2)], and bis[trichlorogold(III)] [DPPE(Au2Cl6)], complexes have in vivo antitumor activity. To determine if interaction with metals in situ can play a role in the antitumor activity of DPPE, we have studied the effects of DPPE
David P Temelkoff et al.
Carbohydrate research, 341(10), 1645-1656 (2006-02-28)
Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from D-glucose and D-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, however, the byproduct phosphine oxide is easily removed
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