696668

Sigma-Aldrich

Nickel(II) chloride ethylene glycol dimethyl ether complex

98%

Synonym(s):
Dichloro(dimethoxyethane)nickel, NiCl2 glyme
Linear Formula:
NiCl2:CH3OCH2CH2OCH3
CAS Number:
Molecular Weight:
219.72
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

98%

reaction suitability

core: nickel
reagent type: catalyst

mp

>300 °C

SMILES string

Cl[Ni]Cl.COCCOC

InChI

1S/C4H10O2.2ClH.Ni/c1-5-3-4-6-2;;;/h3-4H2,1-2H3;2*1H;/q;;;+2/p-2

InChI key

OCMNCWNTDDVHFK-UHFFFAOYSA-L

Application

Nickel(II) chloride ethylene glycol dimethyl ether complex can be used:
  • As a catalyst for the borylation of racemic benzylic chloride to synthesize enantioenriched benzylic boronic esters.
  • As a promoter for the trifluoromethylation of alkyl iodides to synthesize broad range of alkyl-CF3 compounds.
  • For the synthesis of nickel bis(benzimidazol-2-ylidene) pincer complexes which can be used for electrocatalytic reduction of CO2 to CO.
  • As a Lewis acid catalyst for C-acylation β-ketoesters through photoactivation by visible light.

Packaging

1, 5 g in glass bottle

signalword

Danger

hazcat

Acute Tox. 3 Oral - Aquatic Acute 1 - Carc. 1B - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Water-react. 2

storage_class_code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni?s Reagent.
Chen Y, et al.
Organic Letters, 20(15), 4677-4680 (2018)
Synthesis and comparison of nickel, palladium, and platinum bis (N-heterocyclic carbene) pincer complexes for electrocatalytic CO 2 reduction.
Therrien JA, et al.
Dalton Transactions, 47(6), 1827-1840 (2018)
Catalyst-Controlled Regioselective Acylation of ?-Ketoesters with ?-Diazo Ketones Induced by Visible Light.
Liu D, et al.
Organic Letters, 20(22), 7278-7282 (2018)
Amanda Grass et al.
Dalton transactions (Cambridge, England : 2003), 50(7), 2501-2509 (2021-01-31)
Reaction of LiOCtBu2Ph with TlPF6 forms the dimeric Tl2(OCtBu2Ph)2 complex, a rare example of a homoleptic thallium alkoxide complex demonstrating formally two-coordinate metal centers. Characterization of Tl2(OCtBu2Ph)2 by 1H and 13C NMR spectroscopy and X-ray crystallography reveals the presence of...
Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.
Wang Z, et al.
Angewandte Chemie (International Edition in English), 57(44), 14529-14532 (2018)

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