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910724

Sigma-Aldrich

PhPAd-DalPhos

≥95%

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

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Assay

≥95%

form

powder

reaction suitability

reagent type: ligand

mp

193-194 °C

functional group

phosphine

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

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    Substituted cyclopropanes. 5. 1-Cyanocyclopropanecarboxylic acid.
    Jones PG and Schrumpf G.
    Acta Crystallographica Section C, Structural Chemistry, 43(8), 1576-1579 (1987)
    Homoconjugate Addition of Nucleophiles to Cyclopropane-1, 1-Dicarboxylate Derivatives: 2-Oxo-1-Phenyl-3-Pyrrolidinecarboxylic Acid.
    Singh RK and Danishefsky S.
    Organic Syntheses, 66-66 null
    Andrew J Kennedy et al.
    Journal of medicinal chemistry, 54(10), 3524-3548 (2011-04-19)
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