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Merck
CN

910732

CyPAd-DalPhos

≥95%, powder

Synonym(s):

8-(2-(Dicyclohexylphosphaneyl)phenyl)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane

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About This Item

Empirical Formula (Hill Notation):
C28H42O3P2
CAS Number:
1902911-41-4
Molecular Weight:
488.58
MDL number:
MFCD32672281
UNSPSC Code:
12352112
NACRES:
NA.22

Key Documents

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Product Name

CyPAd-DalPhos, ≥95%

SMILES string

P4(C5(OC6(OC(OC4(C6)C)(C5)C)C)C)c1c(cccc1)P(C3CCCCC3)C2CCCCC2

InChI key

RDFYIHPJEXXODP-UHFFFAOYSA-N

InChI

1S/C28H42O3P2/c1-25-19-27(3)31-26(2,29-25)20-28(4,30-25)33(27)24-18-12-11-17-23(24)32(21-13-7-5-8-14-21)22-15-9-6-10-16-22/h11-12,17-18,21-22H,5-10,13-16,19-20H2,1-4H3

assay

≥95%

form

powder

reaction suitability

reagent type: ligand

mp

181-182 °C

functional group

phosphine

Related Categories

Application

CyPAd-DalPhos is ligand developed in the Stradiotto lab that when combined with a Ni(II) source forms an air stable pre catalyst for C(sp2)-O coupling and N-arylation reactions.

Other Notes

Technology Spotlight: DalPhos ligands

Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design

Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room Temperature

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR0300
SHBR0026

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Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room Temperature
Tassone J P, et al
ACS Catalysis, 7(9), 6048-6059 (2017)
Christopher M Lavoie et al.
Nature communications, 7, 11073-11073 (2016-03-24)
Palladium-catalysed C(sp(2))-N cross-coupling (that is, Buchwald-Hartwig amination) is employed widely in synthetic chemistry, including in the pharmaceutical industry, for the synthesis of (hetero)aniline derivatives. However, the cost and relative scarcity of palladium provides motivation for the development of alternative, more

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