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223387

Sigma-Aldrich

Nickel(II) chloride hexahydrate

ReagentPlus®

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About This Item

Linear Formula:
NiCl2 · 6H2O
CAS Number:
7791-20-0
Molecular Weight:
237.69
MDL number:
MFCD00149809
UNSPSC Code:
12352302
PubChem Substance ID:
329752304
NACRES:
NA.55
form:
powder or crystals

Quality Level

100
200

product line

ReagentPlus®

form

powder or crystals

concentration

23.0-26.0% Ni (EDTA titration)

SMILES string

[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].Cl[Ni]Cl

InChI

1S/2ClH.Ni.6H2O/h2*1H;;6*1H2/q;;+2;;;;;;/p-2

InChI key

LAIZPRYFQUWUBN-UHFFFAOYSA-L

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General description

Nickel(II) chloride hexahydrate is a hydrated nickel salt. Its crystals were monoclinc and crystal structure was investigated by X-ray single crystal method.

Application

Nickel(II) chloride hexahydrate may be employed as a catalyst in the high yield synthesis of tetra-substituted pyrrole derivatives. It may be used for the conversion of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers to the corresponding hydroxyl compounds.
Nickel(II) chloride hexahydrate may be used as a catalyst in the following processes:
  • Synthesis of tetra-substituted pyrrole derivatives via four-component condensation reaction of aromatic aldehydes, benzylamines, β-ketoesters and nitroalkanes.
  • In combination with 1,2-ethanedithiol for the deprotection of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers to their corresponding hydroxyl compounds.
  • Synthesis of 3,4-dihydropyrimidinones from aldehydes and β-keto esters via Biginelli condensation.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A Inhalation - Muta. 2 - Repr. 1B - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1 Inhalation

Target Organs

Lungs

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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

223387-BULK:
223387-VAR:
223387-500G:4548173293752
2540054:
223387-VAR-D:
223387-2KG:4548173293745
223387-25G:4548173293738
223387-RSAMPLE:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1731
BCCG4504
BCCG4503
MKCP1860
MKCN9743

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Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones.
Lu J and Bai Y.
Synthesis, 2002(04), 0466-0470 (2002)
A catalytic amount of nickel (II) chloride hexahydrate and 1, 2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers.
Khan AT, et al.
Tetrahedron Letters, 45(52), 9617-9621 (2004)
The Crystal Structure of Nickel Chloride Hexahydrate, NiCl2.6H2O.
Mizuno J.
Journal of the Physical Society of Japan, 16(8), 1571-1580 (1961)
Synthesis of tetra-substituted pyrroles, a potential phosphodiesterase 4B inhibitor, through nickel (II) chloride hexahydrate catalyzed one-pot four-component reaction.
Khan AT, et al.
Tetrahedron Letters, 53(32), 4145-4150 (2012)
John M Besser et al.
Environmental toxicology and chemistry, 32(11), 2495-2506 (2013-05-10)
This study evaluated the chronic toxicity of Ni-spiked freshwater sediments to benthic invertebrates. A 2-step spiking procedure (spiking and sediment dilution) and a 2-stage equilibration period (10 wk anaerobic and 1 wk aerobic) were used to spike 8 freshwater sediments with wide
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