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About This Item
Linear Formula:
ICH=CHCO2C2H5
CAS Number:
Molecular Weight:
226.01
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.)
functional group
ester
iodo
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
Signal Word
Warning
Hazard Statements
Precautionary 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
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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)
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