Identification | More | [Name]
Methyl 3-methoxyacrylate | [CAS]
34846-90-7 | [Synonyms]
3-METHOXYACRYLIC ACID METHYL ESTER MAME METHYL 3-METHOXYACRYLATE METHYL TRANS-3-METHOXYACRYLATE Methyl3-methoxyacrylate,99% Methyl 3-methyl-2-propenoate 3-METHOXYACRYLIC ACID METHYL ESTER 95+% (E)-3-Methoxyacrylic acid methyl ester | [EINECS(EC#)]
672-629-4 | [Molecular Formula]
C5H8O3 | [MDL Number]
MFCD00128206 | [Molecular Weight]
116.12 | [MOL File]
34846-90-7.mol |
Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [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. ]
0-6°C | [Water Solubility ]
Soluble in water | [form ]
Liquid | [color ]
Clear colorless | [InChI]
InChI=1S/C5H8O3/c1-7-4-3-5(6)8-2/h3-4H,1-2H3 | [InChIKey]
AUTCCPQKLPMHDN-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C=COC | [CAS DataBase Reference]
34846-90-7(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R43:May cause sensitization by skin contact. | [Safety Statements ]
S24:Avoid contact with skin . S37:Wear suitable gloves . | [RIDADR ]
3334 | [WGK Germany ]
1
| [HS Code ]
29189900 |
Raw materials And Preparation Products | Back Directory | [Raw materials]
Methanol-->METHYL 3,3-DIMETHOXYPROPIONATE-->2-Propenoyl chloride, 3-methoxy-, (2E)- | [Preparation Products]
Methyl 2-aminothiazole-5-carboxylate-->1-ISOPROPYL-5-HYDROXYPYRAZOL-->1-TERT.BUTYL-5-HYDROXYPYRAZOL-->1-Methylpyrazole-->5-Hydroxy-1-methylpyrazole-->methyl 2-bromo-3,3-dimethoxypropanoate-->Methyl 3-Methoxy-3-((4,4,4-trifluoro-3-oxobut-1-en-1-yl)aMino)propanoate-->Methyl 1-(Pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate-->1H-1,2,3-Triazole-4-carboxylic acid, 1-(1-naphthalenyl)-, methyl ester |
Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS LIQUID | [Uses]
Methyl trans-3-methoxyacrylate is a natural β-?methoxyacrylate which inhibits mitochondrial respiration and exhibits fungicidal activity. | [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]
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 [4] Patent: WO2009/56293, 2009, A1. Location in patent: Page/Page column 8 [5] Patent: WO2009/56293, 2009, A1. Location in patent: Page/Page column 8 |
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