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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

296112-2L:
296112-PZ:
296112-100ML:4548173131504
296112-800ML:4548173131511
296112-VAR:
296112-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rhodium-Catalyzed Novel Trifluoromethylation at the α-Position of α, β-Unsaturated Ketones
Sato K, et al.
Organic Letters, 6(23), 4359-4361 (2004)
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)
Organic Syntheses, 83, 177-177 (2006)
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