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Merck
CN

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:
329761924
UNSPSC Code:
12352103
MDL number:
MFCD11656062

Key Documents

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Product Name

Bis(2,2,6,6-tetramethylpiperidinyl)zinc, 0.5 M in toluene

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9386
SHBP3955
SHBP3790
SHBL1331
SHBJ4860

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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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