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911828

Sigma-Aldrich

PhPAd-DalPhos Ni(o-tolyl)Cl

≥95%

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
UNSPSC Code:
12161600
NACRES:
NA.22

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

235-248 °C

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

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

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Signal Word

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 Code

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

Certificates of Analysis (COA)

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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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