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697486

Sigma-Aldrich

Bis(2,2,6,6-tetramethylpiperidinyl)zinc

0.5 M in toluene

Synonym(s):

Zn(tmp)2

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About This Item

Empirical Formula (Hill Notation):
C18H36N2Zn
Molecular Weight:
345.88
MDL number:
MFCD11656062
UNSPSC Code:
12352103
PubChem Substance ID:
329761924
NACRES:
NA.22

form

liquid

concentration

0.5 M in toluene

density

0.877 g/mL at 25 °C

SMILES string

CC1(C)CCCC(C)(C)N1[Zn]N2C(C)(C)CCCC2(C)C

InChI

1S/2C9H18N.Zn/c2*1-8(2)6-5-7-9(3,4)10-8;/h2*5-7H2,1-4H3;/q2*-1;+2

InChI key

ZWDZFMQAIVHFHF-UHFFFAOYSA-N

Application

Veratile base used for the synthesis of organozinc.[1]

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 Inhalation - STOT SE 3

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

50.0 °F - closed cup

flash_point_c

10 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9386
SHBP3955
SHBP3790
SHBL1331
SHBJ4860

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Pengpeng Zhang et al.
Journal of the American Chemical Society, 142(4), 1757-1762 (2019-12-19)
This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with
David Huang et al.
Journal of the American Chemical Society, 141(14), 5669-5674 (2019-03-13)
We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction
David Huang et al.
Organic letters, 20(3), 684-687 (2018-01-13)
The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and
Hlavinka, M. L.; Hagadorn, J. R.
Organometallics, 26, 4105-4105 (2007)
David Huang et al.
Journal of the American Chemical Society, 141(41), 16249-16254 (2019-09-27)
This report demonstrates the possibility of a nickel-catalyzed difunctionalization of unactivated alkenes initiated by an unstabilized enolate nucleophile. The process tolerates a diverse range of electrophiles, including aryl, heteroaryl, alkenyl, and amino electrophiles. An electron-deficient phosphine ligand and a tetrabutylammonium
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