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Key Documents

220809

Sigma-Aldrich

Diethylzinc solution

15 wt. % in toluene

Synonym(s):

Zincdiethyl

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About This Item

Linear Formula:
(C2H5)2Zn
CAS Number:
Molecular Weight:
123.51
Beilstein:
3587207
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

15 wt. % in toluene

density

0.915 g/mL at 25 °C

SMILES string

CC[Zn]CC

InChI

1S/2C2H5.Zn/c2*1-2;/h2*1H2,2H3;

InChI key

HQWPLXHWEZZGKY-UHFFFAOYSA-N

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Application

Employed together with CF3I in a Rh(I) catalyzed preparation of α-trifluoromethyl ketones from α,ß-unsaturated ketones. Promoter for the Wittig reaction of carbonyl compounds with dibromofluoroacetate and triphenylphosphine leading to α-fluroroacrylates. Ni catalyzed coupling with cyclic anhydrides.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

44.6 °F - closed cup

Flash Point(C)

7 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Alkene-directed regioselective nickel-catalyzed cross-coupling of cyclic anhydrides with diorganozinc reagents.
Rebecca L Rogers et al.
Angewandte Chemie (International ed. in English), 46(48), 9301-9304 (2007-11-07)
Synthesis, 3409-3409 (2006)
Organic Syntheses, 83, 177-177 (2006)
Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral alpha-amino amides.
M Isabel Burguete et al.
Angewandte Chemie (International ed. in English), 46(47), 9002-9005 (2007-09-26)
Abu Bakar Md et al.
Chemical & pharmaceutical bulletin, 56(1), 57-59 (2008-01-08)
N-Heterocyclic carbenes (NHCs) were generated in-situ from imidazolium and imidazolinium salts by deprotonation of C-2 hydrogen and were used as ligands in the copper-catalyzed addition of diethylzinc to N-sulfonylimines. The copper-NHC complexes were shown to possess an efficient ligand acceleration

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