Skip to Content
Merck
All Photos(1)

Documents

498491

Sigma-Aldrich

4-Ethoxy-4-oxobutylzinc bromide solution

0.5 M in THF

Synonym(s):

(4-Ethoxy-4-oxobutyl)zinc(II) bromide, Bromo[4-ethoxy-4-(oxo-κO)butyl-κC]zinc

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
C2H5O2C(CH2)3ZnBr
CAS Number:
Molecular Weight:
260.44
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

0.5 M in THF

density

0.976 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CCOC(=O)CCC[Zn]Br

InChI

1S/C6H11O2.BrH.Zn/c1-3-5-6(7)8-4-2;;/h1,3-5H2,2H3;1H;/q;;+1/p-1

InChI key

QRIVZBPOANGBFR-UHFFFAOYSA-M

Application

4-Ethoxy-4-oxobutylzinc bromide can be used:
  • As an intermediate in one of the key synthetic steps for the preparation of acrylic acid derivatives as EP3 receptor antagonists.
  • As an intermediate in the final step of the total synthesis of a natural product mucosin.
  • As a substrate in the synthesis of multi-substituted haloalkenes by reacting with 1-haloalkenes via Negishi cross-coupling reaction.

Legal Information

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

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-6.2 °F - (THF)

Flash Point(C)

-21.2 °C - (THF)


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’.

Already Own This Product?

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

Visit the Document Library

Total Synthesis of (-)-Mucosin and Revision of Structure
Nolsoe JMJ, et al.
The Journal of Organic Chemistry, 83(24), 15066-15076 (2018)
Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides
Andrei D and Wnuk SF
The Journal of Organic Chemistry, 71(1), 405-408 (2006)
Discovery of a series of acrylic acids and their derivatives as chemical leads for selective EP3 receptor antagonists
Asada M, et al.
Bioorganic & Medicinal Chemistry, 17(18), 6567-6582 (2009)
Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin
Antonsen SG, et al.
Molecules (Basel), 22(10), 1720-1720 (2017)

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