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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:
Molecular Weight:
398.42
Beilstein:
761261
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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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

Signal Word

Warning

Hazard Statements

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)

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Gleb A Silantyev et al.
Inorganic chemistry, 52(4), 1787-1797 (2013-01-30)
The combination of variable temperature (190-297 K) IR and NMR spectroscopy studies with quantum-chemical calculations at the DFT/B3PW91 and AIM level had the aim to determine the mechanism of proton transfer to CpRuH(dppe) (1, dppe = Ph(2)P(CH(2))(2)PPh(2)) and the structures
Anne Westphal et al.
Inorganic chemistry, 51(10), 5748-5763 (2012-05-03)
The molybdenum(V) complex [Mo(O)Cl(3)dppe] [dppe = 1,2-bis(diphenylphosphino)ethane] is considered as a model system for a combined study of the electronic structure using UV/vis absorption and magnetic circular dichroism (MCD) spectroscopy. In order to determine the signs and MCD C-term intensities
Nusrat J Sanghamitra et al.
Journal of medicinal chemistry, 48(4), 977-985 (2005-02-18)
The cytotoxic properties of arylphosphines are regulated by metals. We have synthesized a series of copper(I) complexes of 1,2-bis(diphenylphosphino)ethane (DPPE) and tested their in vitro cytotoxicity in a human lung carcinoma cell line H460. One of the complexes [Cu(2)(DPPE)(3)(CH(3)CN)(2)](ClO(4))(2) (C1)
Organometallics, 12, 3468-3468 (1993)
G D Hoke et al.
Molecular pharmacology, 39(1), 90-97 (1991-01-01)
Bis(diphenylphosphine)ethane (DPPE) and its gold coordination complexes have demonstrated antitumor activity in transplantable tumor models. This report describes the development of a P388 cell line (P388/DPPEc) that is resistant to DPPE and its analogues and the in vitro characterization of

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