Skip to Content
MilliporeSigma
All Photos(1)

Documents

423602

Sigma-Aldrich

Ethyl cis-3-iodoacrylate

98%

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

About This Item

Linear Formula:
ICH=CHCO2C2H5
CAS Number:
31930-36-6
Molecular Weight:
226.01
MDL number:
MFCD00209584
UNSPSC Code:
12352100
PubChem Substance ID:
24866512
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

Related Categories

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

210.2 °F - closed cup

flash_point_c

99 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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

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)
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)
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