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376728

Sigma-Aldrich

Ethylenebis(diphenylphosphine)

99%

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:
24863460
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

Assay

99%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3162
MKCP9037
1438249V
1438249
1435915

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C K Mirabelli et al.
Journal of medicinal chemistry, 30(12), 2181-2190 (1987-12-01)
Bisphosphines related to bis(diphenylphosphino)ethane (dppe) and their gold complexes are described that are active in a spectrum of transplantable tumor models. When administered ip on days 1-5 at its maximally tolerated dose (MTD) of 40 mumol/kg, dppe reproducibly gives 100%
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
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)
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
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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