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761311

Sigma-Aldrich

cataCXium® A Pd G2

Synonym(s):

cataCXium A-Pd-G2, Chloro[(di(1-adamantyl)-N-butylphosphine)-2-(2-aminobiphenyl)]palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C36H49ClNPPd
CAS Number:
1375477-29-4
Molecular Weight:
668.63
MDL number:
MFCD22200549
UNSPSC Code:
12352300
PubChem Substance ID:
329766924
NACRES:
NA.22

form

solid

Quality Level

100

feature

generation 2

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: catalyst
reaction type: Cross Couplings

mp

220 °C (decomposition)

functional group

amine
phosphine

SMILES string

Nc1ccccc1-c2ccccc2[Pd]Cl.CCCCP([C@@]34C[C@@H]5C[C@@H](C[C@@H](C5)C3)C4)[C@@]67C[C@@H]8C[C@@H](C[C@@H](C8)C6)C7

InChI

1S/C24H39P.C12H10N.ClH.Pd/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;/h17-22H,2-16H2,1H3;1-6,8-9H,13H2;1H;/q;;;+1/p-1/t17-,18+,19-,20-,21+,22-,23-,24-;;;

InChI key

CAVPLNLGXHYGIR-DVBMAMJVSA-M

Application

cataCXium® A Pd G2 is a Buchwald′s second generation catalyst that can be used as a palladium source for the coupling of potassium 1-(benzyloxy)alkyltrifluoroborates with aryl and heteroaryl chlorides via Suzuki-Miyaura reaction to yield protected secondary alcohols.

Legal Information

cataCXium is a registered trademark of Umicore AG & Co. KG

related product

Product No.
Description
Pricing

903728

DavePhos Pd G2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

761311-BULK:
761311-5G:4548173311876
761311-250MG:4548173311869
761311-VAR:
761311-1G:4548173311852

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM8321
SHBL9523
SHBJ6995
SHBJ1747
SHBH5076V

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Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy) alkyltrifluoroborates
Molander GA and Wisniewski SR
Journal of the American Chemical Society, 134(40), 16856-16868 (2012)

Articles

2nd Generation Buchwald Precatalysts

Buchwald precatalysts and ligands are bulky electron-rich dialkylbiaryl phospine-based catalysts and structurally related ligands that improve reactivity in Pd-catalyzed cross - coupling reactions

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