944-99-0

Basic information

• Product Name: 2,6-DIMETHOXYPHENYLACETATE
• Synonyms: 2,6-DIMETHOXYPHENYLACETATE;2,6-Dimethoxyphenol acetate;Acetic acid 2,6-dimethoxyphenyl ester;(2,6-dimethoxyphenyl) ethanoate
• CAS NO: 944-99-0
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Product Categories: Aromatic Esters
• Mol File: 944-99-0.mol

Chemical Properties

• Melting Point: 53.5 °C
• Boiling Point: 228.8°Cat760mmHg
• Flash Point: 91.4°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.0719mmHg at 25°C
• Refractive Index: 1.493
• CAS DataBase Reference: 2,6-DIMETHOXYPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHOXYPHENYLACETATE(944-99-0)
• EPA Substance Registry System: 2,6-DIMETHOXYPHENYLACETATE(944-99-0)

Safety Data

• Hazardous Substances Data: 944-99-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-DIMETHOXYPHENYLACETATE is used as a starting material for the synthesis of various pharmaceuticals, particularly cardiovascular drugs. Its unique structure and properties contribute to the development of effective medications for heart-related conditions.
Used in Organic Chemistry:
2,6-DIMETHOXYPHENYLACETATE is used as a building block in the synthesis of natural products and other bioactive compounds. Its versatile chemical structure allows for the creation of a wide range of organic compounds with potential applications in various fields.
Used in Medicinal Chemistry:
Due to its structural and pharmacological properties, 2,6-DIMETHOXYPHENYLACETATE has potential applications in the field of medicinal chemistry. It can be utilized in the design and synthesis of new drugs and therapeutic agents, contributing to advancements in medical treatments.

InChI:InChI=1/C10H12O4/c1-7(11)14-10-8(12-2)5-4-6-9(10)13-3/h4-6H,1-3H3

Upstream product

• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 7664-93-9 sulfuric acid 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 634-36-6 1,2,3-trimethoxybenzene 
• 201230-82-2 carbon monoxide 
• 74-88-4 methyl iodide 

Downstream Products

• 708-53-2 2,3-dihydroxy-4-methoxyacetophenone 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 80894-07-1 2-acetoxy-1,3-dimethoxy-4-nitro-benzene 
• 122756-28-9 3-acetoxy-2,4-dimethoxy-1,5-dinitro-benzene 
• 63604-86-4 1-(3-acetoxy-2,4-dimethoxy-phenyl)-ethanone 
• 90794-39-1 3-acetoxy-2,4-dimethoxyiodobenzene 
• 155593-13-8 3-chlorosyringol acetate 
• 105250-73-5 3,5-dichlorosyringol acetate 
• 18113-22-9 3-chloro-2,6-dimethoxyphenol 
• 78782-46-4 3,5-dichlorosyringol 
• 102872-41-3 1,2,3-trimethoxy-4-nitro-benzene 
• 32904-64-6 2,6-Dimethoxy-3-nitro-phenol 
• 80894-08-2 acetic acid-(3-amino-2,6-dimethoxy-phenyl ester) 

Relevant articles and documents

An efficient method to prepare aryl acetates by the carbonylation of aryl methyl ethers or phenols

Synthesis of valuable chemicals from lignin based compounds is critical for the application of biomass. Here, we develop a method of preparing aryl acetates by the carbonylation of aryl methyl ethers or phenols under low CO pressure. Good to excellent yields of aryl acetates were obtained using different substrates, and a possible reaction mechanism was proposed by conducting a series of control experiments. This method may provide a potential way for the utilization of lignin.

Synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one

The invention relates to a synthesis method of 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one. The synthesis method is characterized by comprising the following steps: removing a 2-methyl group from 1,2,3-trimethoxybenzene serving as an initial raw material to obtain 2,6-dimethoxyphenol; then carrying out a reaction on 2,6-dimethoxyphenol and an acetyl group to obtain 2,6-dimethoxyphenylacetate; andfinally, rearranging 2,6-dimethoxyphenol to obtain the 1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one. Compared with the prior art, the method adopts non-toxic and environment-friendly materials as rawmaterials, is simple to operate and mild in reaction, does not cause environmental pollution or harm to operators, and is suitable for large-scale production.

Synthetic method of 1,3-substituted Diphenylpropenes

The present invention relates to a method for efficiently synthesizing a natural 1,3-substituted diphenylpropene compound having biological activity. The effective method synthesizes 1,3-substituted diphenylpropene compound 1 to 4 using Friedel-Crafts alk

Syntheses and anti-inflammatory activity of natural 1,3-diarylpropenes

First syntheses of five natural 1,3-diarylpropenes (cinnamylphenols) 2-4, 7, and 8 along with synthesis of two other natural 1,3-diarylpropenes 1 and 5 and E-isomer of mucronulastyrene (6) were achieved by Friedel- Crafts alkylation as a key step. Subsequ

The Baeyer-Villiger oxidation versus aromatic ring hydroxylation: Competing organic peracid oxidation mechanisms explored by multivariate modelling of designed multi-response experiments

Peroxy acids can be used as the terminal oxidant for the Baeyer-Villiger oxidation of acetophenones and for direct ring hydroxylation of methoxy-substituted benzenes. An oxidative system involving 3-chloroperbenzoic acid (mCPBA) and 2,6-dimethoxyacetophenone as model substrate was investigated by means of statistical experimental design, multivariate modelling and response surface methodology. The outcome of the organic peracid oxidation experiments was portrayed by a multi-response matrix consisting of the yields of three different compounds; 2,6-dimethoxyphenyl acetate, 1-(4-hydroxy-2,6-dimethoxy-phenyl)ethanone and 3-hydroxy-2,6-dimethoxy-phenyl acetate. The optimized reaction protocol was utilized to investigate a series of various substituted acetophenones. The overall investigation revealed that both the molecular structure of the acetophenone substrate and the experimental conditions exhibited a substantial impact on whether the oxidation reaction follows the oxygen insertion or direct ring hydroxylation mechanism. An improved protocol for the direct ring hydroxylation was also obtained from the experimental and modelling described herein.

O-acylation of substituted phenols with various alkanoyl chlorides under phase-transfer catalyst conditions

Esterification of several types of mono-and disubstituted phenols with various mono-and dialkanoyl chlorides was performed in phase-transfer catalysis conditions, using tetrabutylammonium chloride in a mixture of aqueous NaOH and dichloromethane. The process is particularly efficient (almost quantitative yields) as well as rapid (only 5 min reaction time, at a temperature of0°C). Taylor & Francis Group, LLC.

Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products

An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group was easier than that of an O-methyl group, regardless of wherever they were meta or para to the carbonyl. Thus selective debenzylation can be achieved for substrates bearing both benzyloxy and methoxy groups.

Synthesis of methoxy-substituted phenols by peracid oxidation of the aromatic ring

A novel benign protocol for the preparation of hydroxy-methoxybenzene derivatives is disclosed. By utilizing this protocol, activated aromatic compounds such as l,3-dimethoxy-2-methyl-benzene and 1-(2,6-dimethoxyphenyl) ethanone are smoothly converted to the corresponding monohydroxylated compound. The reaction can be considered to be a normal aromatic electrophilic substitution reaction, and the regioselectivity for the reaction thus follows the similar rules as for electrophilic substitutions. The protocol is composed by benign reagents, namely, hydogenperoxide, acetic acid, and p-toluene sulfonic acid, which lead to the production of ethaneperoxoic acid in situ. The ethaneperoxoic acid operates as the hydroxylating reagent. The hydroxylation reaction is completed within a short period and requires moreover only mild experimental conditions, which make this novel protocol a green, cheap, and rapid process leading to hydroxy-methoxybenzene derivatives. The proposed reaction mechanism is supported by density functional theory and NMR spectroscopy experiments. The mechanism is constituted by two discrete steps: (a) addition of OH+ to the most nucleophilic carbon atom of the aromatic ring, which is the rate-determining step, and (b) the loss of the proton from the aromatic ring.

Preparation of chlorosyringols and chloropyrogallols - Components of pulp bleaching effluents

The preparation and properties of chlorosyringols and chloropyrogallols, components of pulp bleaching effluents, and their acetates are given. The compounds are obtained mainly by direct chlorination of both phenols or of syringol acetate with various chlorinating reagents. 5-Chloropyrogallol and 4,5-dichloropyrogallol were the products of demethylation of 5-chloro-3-methoxycatechol acetate and 4,5-dichloro-3-methoxycatechol acetate, respectively. The acetates of all ten chloro compounds were separated by gas chromatography. Electron impact mass spectra and 1H and 13C NMR data for the acetates are given.