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
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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 Code
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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Hlavinka, M. L.; Hagadorn, J. R.
Organometallics, 26, 4105-4105 (2007)
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
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
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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