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459674

Sigma-Aldrich

Nickel(II) bromide 2-methoxyethyl ether complex

Synonym(s):

Diglyme nickel dibromide

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About This Item

Linear Formula:
NiBr2 · O(CH2CH2OCH3)2
CAS Number:
312696-09-6
Molecular Weight:
352.67
MDL number:
MFCD00274339
UNSPSC Code:
12352302
PubChem Substance ID:
24869583
NACRES:
NA.23

form

powder

reaction suitability

reagent type: catalyst
core: nickel

SMILES string

Br[Ni]Br.COCCOCCOC

InChI

1S/C6H14O3.2BrH.Ni/c1-7-3-5-9-6-4-8-2;;;/h3-6H2,1-2H3;2*1H;/q;;;+2/p-2

InChI key

RRSIMIHTHWYRRA-UHFFFAOYSA-L

application

Nickel(II) bromide 2-methoxyethyl ether complex can be used as a catalyst to prepare:
  • Hindered diarylmethanols and benzylic alcohols by the addition of aryl halides to various aldehydes in the presence of Zn as a reducing agent.
  • Benzene-fused cyclic compounds via reductive dicarbofunctionalization of unactivated alkenes using less reactive benzyl chlorides.
  • Benzylboron derivatives via C-C cross-coupling reaction between substituted 5-bromo-3-methoxy-2-(trimethylsilyl)phenyl triflate and bromomethylboronic acid pinacol ester.
  • N-(Hetero)aryl sulfamides by N-arylation of sulfamides with aryl bromides in the presence of a photosensitizer.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Aryne Reaction and Cross-coupling Approach for the Synthesis of Diverse N-Arylphenylalanine Derivatives
Kobayashi T, et al.
Chemistry Letters (Jpn), 49(7), 809-812 (2020)
Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero) aryl Sulfamides
Simons RT, et al.
The Journal of Organic Chemistry, 85(10), 6380-6391 (2020)
Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols
Garcia KJ, et al.
Journal of the American Chemical Society, 141(5), 1823-1827 (2019)
Nickel-catalyzed asymmetric reductive arylalkylation of unactivated alkenes
Jin Youxiang and Wang Chuan
Angewandte Chemie (International Edition in English), 58(20), 6722-6726 (2019)

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