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696668

Sigma-Aldrich

Nickel(II) chloride ethylene glycol dimethyl ether complex

98%

Synonym(s):

Dichloro(dimethoxyethane)nickel, NiCl2 glyme

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About This Item

Linear Formula:
NiCl2:CH3OCH2CH2OCH3
CAS Number:
29046-78-4
Molecular Weight:
219.72
MDL number:
MFCD00013481
UNSPSC Code:
12161600
PubChem Substance ID:
329761848
NACRES:
NA.22

Assay

98%

form

powder

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

Related Categories

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.

Signal Word

Danger

Hazard Classifications

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Specified Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

696668-5G:4548173923772
696668-BULK:
696668-1G:4548173923765
696668-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
0000409144
0000410248
0000388417
0000367034
0000367034

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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
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)
Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.
Wang Z, et al.
Angewandte Chemie (International Edition in English), 57(44), 14529-14532 (2018)
Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni?s Reagent.
Chen Y, et al.
Organic Letters, 20(15), 4677-4680 (2018)

Articles

Nickel-based Catalysts

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

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