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379670

Sigma-Aldrich

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane

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Synonym(s):
Pd(dppf)Cl2 · CH2Cl2, Pd(dppf)Cl2 · DCM, [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1)
Empirical Formula (Hill Notation):
C35H30Cl4FeP2Pd
CAS Number:
95464-05-4
Molecular Weight:
816.64
MDL number:
MFCD00792899
PubChem Substance ID:
24863679
NACRES:
NA.22

form

solid

Quality Level

200

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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: catalyst

mp

275-280 °C

SMILES string

[Fe].ClCCl.Cl[Pd]Cl.[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6

InChI

1S/2C17H14P.CH2Cl2.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;2-1-3;;;;/h2*1-14H;1H2;2*1H;;/q;;;;;;+2/p-2

InChI key

CWHRHCATIKFSND-UHFFFAOYSA-L

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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Analysis Note

Catalyst employed in the borylation of aryl halides with Bis(pinacolato)diboron(473294) as well as the coupling of the derived arylboronic esters with aryl halides leading to biaryls. Also used in the synthesis of lactams by CO insertion and medium-ring aryl ethers by intramolecular coupling of an aryl halide with an alcohol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - 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

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Tetrahedron, 62, 2006-2006 (2006)
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Journal of the American Chemical Society, 126(20), 6347-6355 (2004-05-20)
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Bryan C Dickinson et al.
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