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Merck
CN

910724

PhPAd-DalPhos

≥95%, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C28H30O3P2
CAS Number:
1902911-39-0
Molecular Weight:
476.48
MDL number:
MFCD32857531
UNSPSC Code:
12352002
NACRES:
NA.22

Key Documents

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Product Name

PhPAd-DalPhos, ≥95%

SMILES string

P4(C5(OC6(OC(OC4(C6)C)(C5)C)C)C)c1c(cccc1)P(c3ccccc3)c2ccccc2

InChI

1S/C28H30O3P2/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/h5-18H,19-20H2,1-4H3

InChI key

SWSJANGQMCPBHH-UHFFFAOYSA-N

assay

≥95%

form

powder

reaction suitability

reagent type: ligand

mp

193-194 °C

functional group

phosphine

Related Categories

Application

PhPAd-DalPhos is ligand developed in the Stradiotto lab that when combined with a Ni(II) source forms an air stable precatalyst for cross coupling of aryl electrophiles with bulky primary amines.

Other Notes

Technology Spotlight: DalPhos ligands

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

PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines

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
SHBS5407

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Probing the Influence of PAd-DalPhos Ancillary Ligand Structure on Nickel-Catalyzed Ammonia Cross-Coupling
Lavoie C M ,et al.
Organometallics, 37(21), 4015-4023 (2018)
Joseph P Tassone et al.
Angewandte Chemie (International ed. in English), 58(8), 2485-2489 (2019-01-04)
The base metal-catalyzed C-N cross-coupling of bulky α,α,α-trisubstituted primary alkylamines with (hetero)aryl electrophiles represents a challenging and under-developed class of transformations that is of significant potential utility, including in the synthesis of lipophilic active pharmaceutical ingredients. Herein, we report that
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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