34846-90-7

Basic information

• Product Name: Methyl 3-methoxyacrylate
• Synonyms: Methyl 3-Methoxyacrylate, 95% 25ML;3-Methoxy Methyl acrylate;Methyle3-methoxyacrylate;METHYL TRANS-3-METHOXYACRYLATE;MAME;METHYL 3-METHOXYACRYLATE;3-METHOXYACRYLIC ACID METHYL ESTER;Methyl3-methoxyacrylate,99%
• CAS NO: 34846-90-7
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• EINECS: 412-900-4
• Mol File: 34846-90-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 3-4°C
• Boiling Point: 56 °C18 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless/Liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.05mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: Methyl 3-methoxyacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-methoxyacrylate(34846-90-7)
• EPA Substance Registry System: Methyl 3-methoxyacrylate(34846-90-7)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37/38
• Safety Statements: 24-37-37/39-26
• RIDADR: 3334
• WGK Germany: 1
• Hazardous Substances Data: 34846-90-7(Hazardous Substances Data)

Usage

Description

Methyl 3-methoxyacrylate, also known as Methyl trans-3-methoxyacrylate, is a natural β-methoxyacrylate characterized by its clear, colorless liquid appearance. It possesses unique chemical properties that enable it to inhibit mitochondrial respiration and exhibit fungicidal activity, making it a valuable compound in various applications.

Uses

Used in Agricultural Industry:
Methyl 3-methoxyacrylate is used as a fungicide for its fungicidal activity, providing protection against various fungal infections in crops and plants. Its natural origin and effectiveness in inhibiting mitochondrial respiration contribute to its potential as a sustainable and environmentally friendly alternative to synthetic fungicides.
Used in Pharmaceutical Industry:
Methyl 3-methoxyacrylate is used as a research compound for its ability to inhibit mitochondrial respiration. This property makes it a valuable tool in studying the mechanisms of cellular respiration and the development of novel therapeutic strategies targeting mitochondrial function in various diseases, including cancer and neurodegenerative disorders.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 48, 1980 DOI: 10.1021/jo01289a012Tetrahedron Letters, 24, p. 5209, 1983 DOI: 10.1016/S0040-4039(00)88398-7

InChI:InChI=1/C5H8O3/c1-7-4-3-5(6)8-2/h3-4H,1-2H3/b4-3+

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 74-86-2 acetylene 
• 63857-17-0 methyl 3-oxopropionate 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 1066-26-8 sodium acetylide 
• 67-56-1 methanol 
• 292638-85-8 acrylic acid methyl ester 
• 463-51-4 Ketene 
• 149-73-5 trimethyl orthoformate 
• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 60778-73-6 β-methoxyacrylic acid chloride 
• 107-31-3 Methyl formate 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 6214-29-5 3-methoxy-2-propen-1-oic acid 
• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 215610-30-3 3-methoxy-1H-pyrazole 
• 60092-92-4 3-(4-nitrophenyl)-4-methoxycarbonylisoxazole 
• 839718-33-1 methyl 3-(4-iodophenyl)isoxazole-4-carboxylate 
• 839718-18-2 methyl 3-(4-(2-chloroethyl)phenyl)isoxazole-4-carboxylate 
• 839718-03-5 methyl 3-(4-chloromethylphenyl)isoxazole-4-carboxylate 
• 2672-58-4 1,3,5-tris-(methoxycarbonyl)benzene 
• 66-22-8 uracil 

Relevant articles and documents

Research and development of the catalytic oxidation of methylacrylate to 3,3-dimethoxy methyl propionate

A selective synthesis of 3,3-dimethoxy methyl propionate has been developed using a green approach, in which the key step is a palladium-catalyzed oxidation of methylacrylate in methanol using oxygen as oxidant. The relationship between several reaction p

Preparation method of methyl 3-methoxyacrylate

The invention discloses a preparation method of methyl 3-methoxyacrylate. The preparation method comprises the steps: taking saturated monocarboxylic ester as a raw material and saturated carboxylic ester as an auxiliary material, and introducing formyl by utilizing methyl formate under the action of a catalyst; carrying out aldol condensation reaction with methanol under the condition that the ionic liquid is used as a catalyst, to obtain methyl 3,3-dimethoxypropionate; after the reaction is completed, separating methanol under reduced pressure, after separation is completed, increasing the temperature to 80-150 DEG C, carrying out an elimination reaction to remove one molecule of methanol on methyl 3,3-dimethoxypropionate, and thus obtaining methyl 3-methoxyacrylate, wherein methyl formate can be replaced with CO, and the raw material cost is lower. The method has the advantages of simple operation, easily available raw materials, high conversion rate, safety, environmental protection and low cost, and can realize industrial production.

Method for preparing E-alkoxyacrylate through one-pot synthesis technology

The invention discloses a method for preparing E-alkoxyacrylate through a one-pot synthesis technology. The method comprises the following steps: S1, carrying out a Friedel-Crafts reaction on alkenylether and oxalyl chloride; S2, decarboxylating a Friedel-Crafts reaction product obtained in step S1 to obtain alkenyl acyl chloride; and S3, esterifying the alkenyl acyl chloride to obtain the E-alkoxyacrylate. The alkenyl ether and oxalyl chloride undergo the Friedel-Crafts reaction at a low temperature under solvent-free and metal catalyst-free conditions, the Friedel-Crafts reaction product undergoes heating decarboxylation to obtain the alkenyl acyl chloride, and the alkenyl acyl chloride is esterified to obtain the E-alkoxyacrylate, so precious metal catalysts and a lot of solvents are not used in the whole technologic route, and severely toxic phosgene and expensive initial raw materials are avoided, thereby the technologic route has the cost advantage in industrial amplified production.