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Merck
CN

911828

PhPAd-DalPhos Ni(o-tolyl)Cl

≥95%, powder

Synonym(s):

(SP-4-3)-Chloro[8-[2-(diphenylphosphino-κP)phenyl]-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane-κP8](2-methylphenyl)nickel

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About This Item

Empirical Formula (Hill Notation):
C35H37ClNiO3P2
CAS Number:
2290490-29-6
Molecular Weight:
661.76
MDL number:
MFCD34166230
UNSPSC Code:
12161600
NACRES:
NA.22

Key Documents

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Product Name

PhPAd-DalPhos Ni(o-tolyl)Cl, ≥95%

SMILES string

Cl[Ni]1(P(C(C2)(O3)C)(C4=CC=CC=C4P(C5=CC=CC=C5)1C6=CC=CC=C6)[C@@](C[C@]3(OC27C)C)(O7)C)C(C=CC=C8)=C8C

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

235-248 °C

Related Categories

Application

PhPAd-DalPhos Ni(o-tolyl)Cl is an air stable precatalyst developed in the Stradiotto lab used for coupling of bulky primary amines with arenes.

Other Notes

Technology Spotlight: DalPhos ligands

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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Muta. 2 - Repr. 2 - Resp. Sens. 1 - STOT RE 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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

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