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Methyl 3-methoxyacrylate

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Methyl 3-methoxyacrylate manufacturers

Methyl 3-methoxyacrylate Basic information
Product Name:Methyl 3-methoxyacrylate
Synonyms:Methyl 3-Methoxyacrylate, 95% 25ML;3-Methoxy Methyl acrylate;MAME;METHYL 3-METHOXYACRYLATE;Methyle3-methoxyacrylate;3-METHOXYACRYLIC ACID METHYL ESTER;Methyl3-methoxyacrylate,99%;Methyl 3-methyl-2-propenoate
CAS:34846-90-7
MF:C5H8O3
MW:116.12
EINECS:672-629-4
Product Categories:
Mol File:34846-90-7.mol
Methyl 3-methoxyacrylate Structure
Methyl 3-methoxyacrylate Chemical Properties
Melting point 3-4°C
Boiling point 56 °C18 mm Hg(lit.)
density 1.08 g/mL at 25 °C(lit.)
refractive index n20/D 1.451(lit.)
Fp 145 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
Water Solubility Soluble in water
form Liquid
color Clear colorless
InChIInChI=1S/C5H8O3/c1-7-4-3-5(6)8-2/h3-4H,1-2H3
InChIKeyAUTCCPQKLPMHDN-UHFFFAOYSA-N
SMILESC(OC)(=O)C=COC
CAS DataBase Reference34846-90-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 43-36/37/38
Safety Statements 24-37-37/39-26
RIDADR 3334
WGK Germany 1
HS Code 29189900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Methyl 3-methoxyacrylate Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS LIQUID
UsesMethyl trans-3-methoxyacrylate is a natural β-methoxyacrylate which inhibits mitochondrial respiration and exhibits fungicidal activity.
ApplicationMethyl 3-methoxyacrylate is a kind of important medicine and pesticide intermediate, as can be used as the intermediate of sterilant flonicamid.
Synthesis Reference(s)The Journal of Organic Chemistry, 45, p. 48, 1980 DOI: 10.1021/jo01289a012
Tetrahedron Letters, 24, p. 5209, 1983 DOI: 10.1016/S0040-4039(00)88398-7
Synthesis
METHYL 3,3-DIMETHOXYPROPIONATE

7424-91-1

Methyl 3-methoxyacrylate

34846-90-7

The composition of the raw materials of this embodiment: 560 g of methyl acrylate, 716 g of methanol, 2.24 g of cobalt oxide, 8.96 g of indium oxide, and 17.6 g of concentrated sulfuric acid; method of preparation: methyl acrylate, methanol, and a synthesis catalyst (cobalt oxide and indium oxide) were added into a reactor, and the temperature of the reaction solution was maintained at 50 °C with sufficient stirring. Nitrogen and oxygen were charged into the reactor, and the partial pressure of nitrogen and oxygen was controlled to be 0.4 MPa to start the reaction. The reaction lasted for 16 hours. The reaction was judged to be complete when the content of methyl acrylate in the reaction solution decreased to 3%, followed by the addition of etherified reaction product. The catalyst was recovered by filtration, and petroleum ether was added to the filtrate, which was homogeneously stirred and left to stratify. The upper layer was petroleum ether layer, and the petroleum ether was recovered by distillation at atmospheric pressure to obtain the intermediate 3,3-dimethoxypropanoic acid methyl ester 703 g. Methanol and methyl acrylate were recovered from the lower aqueous phase. Methyl 3,3-dimethoxypropionate was transferred to a cracking kettle and 17.6 g of concentrated sulfuric acid was slowly added and the temperature was raised to 190 °C for 20 h of cracking reaction. All the cracking products were collected to obtain 430 g of crude methyl 3-methoxyacrylate (MAME). The crude MAME was placed in a distillation vessel and the product was purified by vacuum distillation, resulting in 478 g of the target product, methyl 3-methoxyacrylate. In this embodiment, the yield based on methyl acrylate was 82.4% and the purity of the product was 95.8%.

References[1] Patent: WO2009/56293, 2009, A1. Location in patent: Page/Page column 8-9
[2] Patent: CN105418421, 2016, A. Location in patent: Paragraph 0020; 0023
[3] Patent: WO2009/56293, 2009, A1. Location in patent: Page/Page column 8
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