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296112

Sigma-Aldrich

Diethylzinc solution

1.0 M in hexanes

Synonym(s):

Zincdiethyl

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About This Item

Linear Formula:
(C2H5)2Zn
CAS Number:
557-20-0
Molecular Weight:
123.51
Beilstein:
3587207
MDL number:
MFCD00009021
UNSPSC Code:
12352103
PubChem Substance ID:
24857838
NACRES:
NA.22

Quality Level

100

concentration

1.0 M in hexanes

density

0.726 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

Diethylzinc solution can be used as a reagent to prepare:
  • α-trifluoromethyl ketones from α, β-unsaturated ketones with Rh (I) catalyst.
  • Alkynylzinc reagents which are used in cross-coupling reactions.
  • Chiral secondary alcohols from aromatic and aliphatic aldehydes in presence of camphor-derived β-amino alcohol.
  • 1, 4 conjugate addition product with enones.
  • α-fluoroacrylates from aldehydes and ketones.

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 1 Inhalation - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Nervous system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-9.4 °F - closed cup

Flash Point(C)

-23 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR5156
STBL4522
SHBP4376
STBK9547
STBK4682

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Enantioselective copper-catalyzed conjugate addition using chiral diaminocarbene ligands
Guillen F, et al.
Tetrahedron Asymmetry, 12(15), 2083-2086 (2001)
Asymmetric addition of diethylzinc to aldehydes catalyzed by a camphor-derived β-amino alcohol
Wu Z-L, et al.
Tetrahedron Asymmetry, 20(13), 1556-1560 (2009)
Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds
Dabdoub MJ, et al.
Tetrahedron Letters, 41(4), 437-440 (2000)
Rhodium-Catalyzed Novel Trifluoromethylation at the α-Position of α, β-Unsaturated Ketones
Sato K, et al.
Organic Letters, 6(23), 4359-4361 (2004)
Organic Syntheses, 83, 177-177 (2006)
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