423602
Ethyl cis-3-iodoacrylate
98%
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About This Item
Linear Formula:
ICH=CHCO2C2H5
CAS Number:
Molecular Weight:
226.01
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Product Name
Ethyl cis-3-iodoacrylate, 98%
InChI
1S/C5H7IO2/c1-2-8-5(7)3-4-6/h3-4H,2H2,1H3/b4-3-
SMILES string
[H]\C(I)=C(/[H])C(=O)OCC
InChI key
AELYFQSZXFFNGP-ARJAWSKDSA-N
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
Quality Level
Related Categories
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
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
Regulatory Information
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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)
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)
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)
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