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900593

Sigma-Aldrich

PAd-DalPhos

95%

Synonym(s):

8-[2-[Bis(2-methylphenyl)phosphino]phenyl]-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane

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250 MG
$394.00

$394.00


Estimated to ship onMarch 28, 2025


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250 MG
$394.00

About This Item

Empirical Formula (Hill Notation):
C30H34O3P2
CAS Number:
Molecular Weight:
504.54
MDL number:
UNSPSC Code:
12161600
NACRES:
NA.22

$394.00


Estimated to ship onMarch 28, 2025


Request a Bulk Order

Quality Level

Assay

95%

form

powder or crystals

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: ligand

functional group

phosphine

SMILES string

P4(C5(OC6(OC(OC4(C6)C)(C5)C)C)C)c1c(cccc1)P(c3c(cccc3)C)c2c(cccc2)C

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reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Heck Reaction, reaction type: Stille Coupling, reagent type: ligand, reaction type: Negishi Coupling

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

reaction suitability

-

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: ligand
reaction type: Cross Couplings

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

form

powder or crystals

form

powder or crystals

form

powder or crystals

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

PAd-DalPhos is a versatile air stable pre-catalyst for C(sp2)-N coupling.[1] It catalyzes N-arylation of amides with (hetero)aryl (pseudo)halide.[2] It can also be used in the synthesis of unsymmetrical 1,3-di(hetero)aryl-1H-indazoles from hydrazine, o-chloro (hetero)benzophenones and (hetero)aryl bromides.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Nickel?Catalyzed N?Arylation of Primary Amides and Lactams with Activated (Hetero) aryl Electrophiles.
Lavoie C M, et al.
Chemistry?A European Journal , 22(52), 18752-18755 (2016)
Ni and Cu-catalyzed one pot synthesis of unsymmetrical 1, 3-di (hetero) aryl-1H-indazoles from hydrazine, o-chloro (hetero) benzophenones, and (hetero) aryl bromides.
Wiethan C, et al.
Organic & Biomolecular Chemistry, 15(23), 5062-5069 (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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