Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

498521

Sigma-Aldrich

3-Ethoxy-3-oxopropylzinc bromide solution

0.5 M in THF

Synonym(s):

(2-Ethoxycarbonylethyl)zinc bromide, (3-Ethoxy-3-oxopropyl)zinc(II)bromide, 3-Ethoxy-3-oxopropylzinc bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C2H5O2CCH2CH2ZnBr
CAS Number:
193065-68-8
Molecular Weight:
246.42
MDL number:
MFCD00671976
UNSPSC Code:
12352103
PubChem Substance ID:
24873205
NACRES:
NA.22

concentration

0.5 M in THF

density

0.972 g/mL at 25 °C

functional group

ester

storage temp.

2-8°C

SMILES string

CCOC(=O)CC[Zn]Br

InChI

1S/C5H9O2.BrH.Zn/c1-3-5(6)7-4-2;;/h1,3-4H2,2H3;1H;/q;;+1/p-1

InChI key

XLKAROLEWCMBDC-UHFFFAOYSA-M

Application

3-Ethoxy-3-oxopropylzinc bromide is a reagent used to insert ethyl propanoate group to the substrate. It can be used in:
  • Synthesis of γ-keto esters from aryl chlorides.
  • Synthesis of sulfones from 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and alkyl halides.
  • Negishi cross-couplings with aryl vinyl phosphates to synthesize 1,1-disubstituted alkenes.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Statements

H225,H302,H314,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17.0 °C - closed cup

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBQ2252
SHBP4036
SHBN6982
SHBN8135
SHBM9591

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of the Novel Tetrahydropyrazolo [3, 4-c] pyridin-5-one Scaffold.
Howe N J, et al.
Synlett, 26(02), 228-232 (2015)
Investigations on the Suzuki? Miyaura and Negishi Couplings with Alkenyl Phosphates: Application to the Synthesis of 1, 1-Disubstituted Alkenes.
Hansen A L, et al.
The Journal of Organic Chemistry, 72(17), 6464-6472 (2007)
Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides.
Rocke B N, et al.
Organic Letters, 16(1), 154-157 (2013)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service