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709042

Sigma-Aldrich

CX31

Umicore, 95%

Synonym(s):

Chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium (II), [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C36H45ClN2Pd
CAS Number:
884879-23-6
Molecular Weight:
647.63
MDL number:
MFCD11045095
UNSPSC Code:
12161600
PubChem Substance ID:
329762845
NACRES:
NA.22

Assay

95%

form

powder

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

205-208 °C

SMILES string

[CH2][CH][CH]c1ccccc1.CC(C)c2cccc(C(C)C)c2N3C=CN(\C3=[Pd]/Cl)c4c(cccc4C(C)C)C(C)C

InChI

1S/C27H36N2.C9H9.ClH.Pd/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;1-2-6-9-7-4-3-5-8-9;;/h9-16,18-21H,1-8H3;2-8H,1H2;1H;/q;;;+1/p-1

InChI key

RWGNZUQSYXTZIX-UHFFFAOYSA-M

Application

  • Catalyst for Suzuki coupling (eq. 1)
  • Catalyst for Buchwald-Hartwig amination reaction (eq. 2)
Catalyst for:
  • Suzuki-Miyaura couplings
  • Buchwald-Hartwig couplings

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

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

Storage Class Code

13 - Non 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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Nicolas Marion et al.
Journal of the American Chemical Society, 128(12), 4101-4111 (2006-03-23)
A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me2, Ph] have been synthesized and fully characterized. When compared to (NHC)Pd(allyl)Cl, substitution at the terminal position of the allyl scaffold favors a more
Bruce H Lipshutz et al.
Organic letters, 10(7), 1333-1336 (2008-03-14)
Use of a dilute aqueous solution containing a nonionic amphiphile allows efficient Suzuki-Miyaura cross-couplings of arylboronic acids with a wide array of aryl halides and pseudohalides, including sterically hindered and lipophilic substrates, in most cases at room temperature.
Oscar Navarro et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(19), 5142-5148 (2006-04-22)
The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal

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