Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

423602

Sigma-Aldrich

Ethyl cis-3-iodoacrylate

98%

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
ICH=CHCO2C2H5
CAS Number:
Molecular Weight:
226.01
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.533 (lit.)

bp

85 °C/20 mmHg (lit.)

density

1.765 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]\C(I)=C(/[H])C(=O)OCC

InChI

1S/C5H7IO2/c1-2-8-5(7)3-4-6/h3-4H,2H2,1H3/b4-3-

InChI key

AELYFQSZXFFNGP-ARJAWSKDSA-N

General description

Ethyl cis-3-iodoacrylate (cis-ethyl-β-iodoacrylate, ethyl (Z)-β-iodoacrylate) is Z-vinyl iodide derivative. It is reported to be prepared from ethyl propiolate by treating with sodium iodide. Its Suzuki coupling reaction with cyclic vinyl boronic acids has been studied.

Application

Ethyl cis-3-iodoacrylate may be used in the synthesis of the following:
  • vinyl sulfides
  • (Z)-1-iodohept-1-en-3-ol
  • (E)-1-iodohept-1-en-3-ol
  • (Z)-β-iodoacrolein
  • 6-oxo-M1Guo

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

Stereo-and regiospecific Cu-catalyzed cross-coupling reaction of vinyl iodides and thiols: a very mild and general route for the synthesis of vinyl sulfides.
Kabir MS, et al.
Organic Letters, 10(15), 3363-3366 (2008)
Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.
Hansen EC and Lee D.
Journal of the American Chemical Society, 128(25), 8142-8143 (2006)
Selection of monoclonal antibodies against 6-oxo-M1dG and their use in an LC-MS/MS assay for the presence of 6-oxo-M1dG in vivo.
Akingbade D, et al.
Chemical Research in Toxicology, 25(2), 454-461 (2012)
A simple and convenient method for the preparation of (Z)-β-iodoacrolein and of (Z)- or (E)-γ-iodo allylic alcohols: (Z)- and (E)-1-iodohept-1-en-3-ol.
Marek I, et al.
Organic Syntheses, 74, 194-194 (1997)

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