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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.

Signal Word

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 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

Certificates of Analysis (COA)

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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
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(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.
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