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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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250 MG

$418.00

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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

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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

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This Item
9190048.18255379506
CyPAd-DalPhos ≥95%

Sigma-Aldrich

910732

CyPAd-DalPhos

AliPhos ≥95%

Sigma-Aldrich

919004

AliPhos

Paraldehyde for synthesis

Sigma-Aldrich

8.18255

Paraldehyde

Tris(2,3-epoxypropyl) isocyanurate

Sigma-Aldrich

379506

Tris(2,3-epoxypropyl) isocyanurate

reaction suitability

reagent type: ligand

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings, reagent type: ligand

reaction suitability

-

reaction suitability

-

assay

≥95%

assay

≥95%

assay

≥98.0% (GC)

assay

-

functional group

phosphine

functional group

phosphine

functional group

-

functional group

-

form

powder

form

powder

form

liquid

form

powder

mp

181-182 °C

mp

-

mp

12 °C

mp

-

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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