(Z)-3-Iodopropenoic acid methyl ester

Base Information

• Chemical Name: (Z)-3-Iodopropenoic acid methyl ester
• CAS No.: 6214-23-9
• Molecular Formula: C4H5IO2
• Molecular Weight: 211.987
• Hs Code.: 2916190090
• European Community (EC) Number: 867-480-9
• DSSTox Substance ID: DTXSID00420163
• Nikkaji Number: J469.869J
• Wikidata: Q82231377
• Mol file: 6214-23-9.mol

Synonyms:6214-23-9;(Z)-3-Iodopropenoic acid methyl ester;(Z)-Methyl 3-iodoacrylate;methyl (Z)-3-iodoprop-2-enoate;(Z)-3-Iodopropenoic acid methyl ester 95/5 Z/E;2-Propenoic acid, 3-iodo, methyl ester, (Z)-;methyl (2Z)-3-iodoprop-2-enoate;MFCD09265518;methyl z-3-iodoacrylate;(Z)-Methyl3-iodoacrylate;(Z)-methyl-3-iodoacrylate;Methyl (Z)-3-iodoproacrylate;SCHEMBL3899170;DTXSID00420163;AKOS015850907;AS-66157;CS-0150951;Z-2-Propenoic acid, 3-iodo-, methyl ester

Chemical Property of (Z)-3-Iodopropenoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.823mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 182.1°C at 760 mmHg
• Flash Point: 63.9°C
• PSA: 26.30000
• Density: 1.918g/cm³
• LogP: 1.10810
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 211.93343
• Heavy Atom Count: 7
• Complexity: 87.7

Purity/Quality:

98%min ^*data from raw suppliers

(Z)-3-Iodopropenoic acid methyl ester 95/5 Z/E ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CI
• Isomeric SMILES: COC(=O)/C=C\I

Technology Process of (Z)-3-Iodopropenoic acid methyl ester

There total 5 articles about (Z)-3-Iodopropenoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

propynoic acid methyl ester (922-67-8) → methyl (2Z)-3-iodoprop-2-enoate (6214-23-9)

Guidance literature:

With sodium iodide; In acetic acid; at 70 ℃;

DOI:10.1021/ja046344x

Reference yield: 99.0%

methanol (67-56-1) + (Z)-3-iodoprop-2-enoic acid (6214-35-3) → methyl (2Z)-3-iodoprop-2-enoate (6214-23-9)

Guidance literature:

With diazomethyl-trimethyl-silane; In toluene; at 0 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b03422

Reference yield: 95.0%

propynoic acid methyl ester (922-67-8) → 3-iodoacrylic acid methyl ester (6213-88-3,6214-23-9,89033-13-6)

Guidance literature:

With acetic acid; sodium iodide; In acetonitrile; at 100 ℃; for 10h; Inert atmosphere;

DOI:10.1002/anie.201004647

upstream raw materials:

methanol

(Z)-3-iodoprop-2-enoic acid

propynoic acid methyl ester

Downstream raw materials:

methyl (2Z,4E)-5-phenylpenta-2,4-dienoate

methyl (2Z,4E)-6-oxohexa-2,4-dienolate

tetra-(n-butyl)ammonium iodide

methyl (E)-3-(diethylamino)-2-propenoate

Refernces

• 1、 Spino, Claude,Rezaei, Hadi,Dupont-Gaudet, Kristina,Belanger, Francis. "Inter- and intramolecular [4 + 1]-cycloadditions between electron-poor dienes and electron-rich carbenes". . p. 9926 - 9927. Retrieved 2004.
• 2、 Chen, Violet Yijang,Kwon, Ohyun. "Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis". supporting information. p. 8874 - 8881. Retrieved 2021/03/17.
• 3、 Artok, Levent,Bilgi, Yasemin,Ku?, Melih. "Palladium-catalysed regio- And stereoselective arylative substitution of γ,δ-epoxy-α,β-unsaturated esters and amides by sodium tetraaryl borates". supporting information. p. 6378 - 6383. Retrieved 2020/09/07.