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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

Quality Level

100

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

Related Categories

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

Signal Word

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 Code

4.1B - Flammable solid hazardous materials

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

459674-5G:4548173319964
459674-10G:
459674-BULK:
459674-25G:
459674-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6325
SHBN6728
SHBM2093
SHBK9081
SHBK0798

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Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero) aryl Sulfamides
Simons RT, et al.
The Journal of Organic Chemistry, 85(10), 6380-6391 (2020)
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)
Nickel-catalyzed asymmetric reductive arylalkylation of unactivated alkenes
Jin Youxiang and Wang Chuan
Angewandte Chemie (International Edition in English), 58(20), 6722-6726 (2019)
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)

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