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673064

Sigma-Aldrich

(2-Methylallyl)palladium(II) chloride dimer

Synonym(s):

Chloro(2-methylallyl)palladium(II) dimer, Dichlorobis(2-methylallyl)dipalladium, NSC 270885

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About This Item

Linear Formula:
[CH2=C(CH3)CH2PdCl]2
CAS Number:
12081-18-4
Molecular Weight:
393.94
MDL number:
MFCD08561141
UNSPSC Code:
12161600
PubChem Substance ID:
24885140
NACRES:
NA.22

form

solid

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

168.2-174.0 °C

storage temp.

2-8°C

SMILES string

Cl[Pd].Cl[Pd].[CH2][C]([CH2])C.[CH2][C]([CH2])C

InChI

1S/2C4H7.2ClH.2Pd/c2*1-4(2)3;;;;/h2*1-2H2,3H3;2*1H;;/q;;;;2*+1/p-2

InChI key

XVIHZVZZPKOMRE-UHFFFAOYSA-L

Application

Catalyst for:
  • Asymmetric allylic alkylation reactions
  • Suzuki-Miyaura reactions
  • Reductive cleavage reactions
  • Reaction of alkenyloxiranes with carbon monoxide

Analysis Note

Precursor to a Pd(I) catalyst used in cross-coupling of organosilanols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC1882
MKBJ2190V
MKBH2972V
05524CE

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Scott E Denmark et al.
Organic letters, 8(4), 793-795 (2006-02-14)
[reaction: see text] Sodium silanolates derived from a number of heterocyclic silanols undergo cross-coupling with a variety of aromatic iodides and bromides under mild conditions. In situ deprotonation of the silanols with an equivalent amount of sodium hydride in toluene

Articles

Organosilanols

Pd-catalyzed cross-coupling of silicon compounds offers an alternative in synthetic chemistry.

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