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917982

Sigma-Aldrich

Tetrapyridyl nickel (ll) dichloride

≥95%

Synonym(s):

(NiCl2(py)4

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About This Item

Empirical Formula (Hill Notation):
C20H20Cl2N4Ni
CAS Number:
14076-99-4
Molecular Weight:
446.00
MDL number:
MFCD34706285
UNSPSC Code:
12352103
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

>300 °C

InChI

1S/4C5H10N.2ClH.Ni/c4*1-2-4-6-5-3-1;;;/h4*1-5H2;2*1H;/q4*-1;;;+6/p-2

InChI key

UOXIEMDYDIZJAZ-UHFFFAOYSA-L

Application

Tetrapyridyl nickel (ll) dichloride is a Ni precatalyst used for a variety of cross-coupling reactions.

Other Notes

Air-Stable Nickel Precatalysts for Fast and Quantitative Cross-Coupling of Aryl Sulfamates with Aryl Neopentylglycolboronates at Room Temperature

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Ryan L Jezorek et al.
Organic letters, 16(24), 6326-6329 (2014-12-04)
A library containing 10 air-stable Ni(II)X(Aryl)(PCy3)2 σ-complexes as precatalysts (X = Cl, Br, OTs, OMs, aryl = 1-naphthyl, 2-naphthyl; X = Cl, 1-acenaphthenyl, 1-(2-methoxynaphthyl), 9-phenanthrenyl, 9-anthracyl) was synthesized and demonstrated to quantitatively cross-couple 2-methoxyphenyl dimethylsulfamate with methyl 4-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)benzoate at 23
Andrés García-Domínguez et al.
Angewandte Chemie (International ed. in English), 58(35), 12286-12290 (2019-06-27)
The potential of merging photoredox and nickel catalysis to perform multicomponent alkene difunctionalizations under visible-light irradiation is demonstrated here. Secondary and tertiary alkyl groups, as well as sulfonyl moieties can be added to the terminal position of the double bond

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