697486
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/2C9H18N.Zn/c2*1-8(2)6-5-7-9(3,4)10-8;/h2*5-7H2,1-4H3;/q2*-1;+2
SMILES string
CC1(C)CCCC(C)(C)N1[Zn]N2C(C)(C)CCCC2(C)C
InChI key
ZWDZFMQAIVHFHF-UHFFFAOYSA-N
form
liquid
concentration
0.5 M in toluene
density
0.877 g/mL at 25 °C
Application
Veratile base used for the synthesis of organozinc.
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
WGK 3
flash_point_f
50.0 °F - closed cup
flash_point_c
10 °C - closed cup
Regulatory Information
易制毒化学品（3类）
危险化学品
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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)
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
Yifeng Chen et al.
Angewandte Chemie (International ed. in English), 56(28), 8258-8262 (2017-06-01)
The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts.
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
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