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802948

Sigma-Aldrich

(dppf)Ni(o-tolyl)Cl

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Synonym(s):
Buchwald Ni Catalyst
Empirical Formula (Hill Notation):
C41H35ClFeNiP2
CAS Number:
Molecular Weight:
739.66
MDL number:
PubChem Substance ID:

assay

95%

Quality Level

form

powder

reaction suitability

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

mp

173 °C

storage temp.

2-8°C

SMILES string

CC1=CC=CC=C1[Ni]Cl.[C]2(P(C3=CC=CC=C3)C4=CC=CC=C4)[C][C][C][C]2.[C]5(P(C6=CC=CC=C6)C7=CC=CC=C7)[C][C][C][C]5.[Fe]

InChI

1S/2C17H14P.C7H7.ClH.Fe.Ni/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;1-7-5-3-2-4-6-7;;;/h2*1-14H;2-5H,1H3;1H;;/q;;;;;+1/p-1

InChI key

LGLPATFHWYLMCO-UHFFFAOYSA-M

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This Item
804398905070919578
(dppf)Ni(o-tolyl)Cl

802948

(dppf)Ni(o-tolyl)Cl

[(TMEDA)Ni(o-tolyl)Cl] 95%

804398

[(TMEDA)Ni(o-tolyl)Cl]

[(TEEDA)Ni(o-tolyl)Cl] ≥95%

905070

[(TEEDA)Ni(o-tolyl)Cl]

PAd2-DalPhos Ni(o-tolyl)Cl

919578

PAd2-DalPhos Ni(o-tolyl)Cl

assay

95%

assay

95%

assay

≥95%

assay

-

form

powder

form

powder

form

powder or crystals

form

powder

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

mp

173 °C

mp

-

mp

>300 °C

mp

>300 °C

General description

(dppf)Ni(o-tolyl)Cl is an air stable reagent. Its crystal structure has been investigated by X-ray studies. (dppf)Ni(o-tolyl)Cl can be prepared from (Ph3P)2Ni(o-tolyl)Cl. It is widely employed as a precatalyst for various C-N bond formation reactions. Efficacy of (dppf)Ni(o-tolyl)Cl as a precatalyst for the amination of 4-n-butylchlorobenzene with morpholine under various optimized reaction conditions has been investigated.

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Muta. 2 - Repr. 1B - Resp. Sens. 1 - Skin Sens. 1 - STOT RE 1 Inhalation

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Nathaniel H Park et al.
Organic letters, 16(1), 220-223 (2013-11-29)
A new air-stable nickel precatalyst for C-N cross-coupling is reported. The developed catalyst system displays a greatly improved substrate scope for C-N bond formation to include both a wide range of aryl and heteroaryl electrophiles and aryl, heteroaryl, and alkylamines.

Articles

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

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