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900593

PAd-DalPhos

95%, powder or crystals

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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About This Item

Empirical Formula (Hill Notation):
C30H34O3P2
CAS Number:
1902911-38-9
Molecular Weight:
504.54
MDL number:
MFCD31381910
UNSPSC Code:
12161600
NACRES:
NA.22
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Product Name

PAd-DalPhos, 95%

Quality Level

100

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

InChI key

RTLXHCKHEDGJLB-UHFFFAOYSA-N

Application

PAd-DalPhos is a versatile air stable pre-catalyst for C(sp2)-N coupling. It catalyzes N-arylation of amides with (hetero)aryl (pseudo)halide. 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.

Storage Class

11 - 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
MKCK6598
MKCK6601

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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)
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)
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

Global Trade Item Number

SKUGTIN
900593-250MG04061833250396