3467-59-2

Basic information

• Product Name: 2',5'-DIMETHOXYACETANILIDE
• Synonyms: 2',5'-DIMETHOXYACETANILIDE;2,5-DIMETHOXYACETANILIDE;2,5-DIMETHOXYACETOANILIDE;2-ACETAMIDO-1,4-DIMETHOXYBENZENE;2,5-dimethyloxyacetanilide;dimethoxyacetoanilide;n-(2,5-dimethoxyphenyl)-acetamid;N-(2,5-dimethoxyphenyl)-Acetamide
• CAS NO: 3467-59-2
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 222-423-1
• Mol File: 3467-59-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 91 °C
• Boiling Point: 346.3°Cat760mmHg
• Flash Point: 163.2°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 5.8E-05mmHg at 25°C
• Refractive Index: 1.544
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2',5'-DIMETHOXYACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-DIMETHOXYACETANILIDE(3467-59-2)
• EPA Substance Registry System: 2',5'-DIMETHOXYACETANILIDE(3467-59-2)

Safety Data

• Hazardous Substances Data: 3467-59-2(Hazardous Substances Data)

Usage

General Description

2',5'-DIMETHOXYACETANILIDE is a chemical compound that belongs to the class of acetanilide derivatives. It is also known by the chemical name N-(2,5-dimethoxyphenyl)acetamide. 2',5'-DIMETHOXYACETANILIDE is commonly used in pharmaceutical research and development due to its potential as an analgesic and anti-inflammatory agent. It has been studied for its potential use in pain management and as a treatment for various inflammatory conditions. However, further research is needed to fully understand its biological activity and potential therapeutic applications. Additionally, 2',5'-DIMETHOXYACETANILIDE may have other industrial or research applications, but its full range of uses and properties are still being explored.

InChI:InChI=1/C10H13NO3/c1-7(12)11-9-6-8(13-2)4-5-10(9)14-3/h4-6H,1-3H3,(H,11,12)

Upstream product

• 75-05-8 acetonitrile 
• 23997-82-2 2,5-dimethoxyphenyl methyl ketone oxime 
• 79-24-3 Nitroethane 
• 150-78-7 1,4-dimethoxybezene 
• 89-39-4 1,4-dimethoxy-2-nitrobenzene 
• 165072-81-1 1-(2,5-dimethoxy)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester 
• 75-36-5 acetyl chloride 
• 102-56-7 2,5-dimethoxyaniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 102-56-7 2,5-dimethoxyaniline 
• 33264-65-2 2,5-dimethoxy-N-phenylaniline 
• 10224-66-5 2,5-dimethoxy-N-methylaniline 
• 1355024-26-8 (2S)-2-((4-acetamido-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)-3-phenylpropanoic acid 

Relevant articles and documents

Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes

A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.

Natural Abenquines and Their Synthetic Analogues Exert Algicidal Activity against Bloom-Forming Cyanobacteria

Abenquines are natural quinones, produced by some Streptomycetes, showing the ability to inhibit cyanobacterial growth in the 1 to 100 μM range. To further elucidate their biological significance, the synthesis of several analogues (4f-h, 5a-h) allowed us to identify some steric and electronic requirements for bioactivity. Replacing the acetyl by a benzoyl group in the quinone core and also changing the amino acid moiety with ethylpyrimidinyl or ethylpyrrolidinyl groups resulted in analogues 25-fold more potent than the natural abenquines. The two most effective analogues inhibited the proliferation of five cyanobacterial strains tested, with IC50 values ranging from 0.3 to 3 μM. These compounds may be useful leads for the development of an effective strategy for the control of cyanobacterial blooms.

Tailoring Natural Abenquines to Inhibit the Photosynthetic Electron Transport through Interaction with the D1 Protein in Photosystem II

Abenquines are natural N-acetylaminobenzoquinones bearing amino acid residues, which act as weak inhibitors of the photosynthetic electron transport chain. Aiming to exploit the abenquine scaffold as a model for the synthesis of new herbicides targeting photosynthesis, 14 new analogues were prepared by replacing the amino acid residue with benzylamines and the acetyl with different acyl groups. The synthesis was accomplished in three steps with a 68-95% overall yield from readily available 2,5-dimethoxyaniline, acyl chlorides, and benzyl amines. Key steps include (i) acylation of the aniline, (ii) oxidation, and (iii) oxidative addition of the benzylamino moiety. The compounds were assayed for their activity as Hill inhibitors, under basal, uncoupled, or phosphorylating conditions, or excluding photosystem I. Four analogues showed high effectiveness (IC50 = 0.1-0.4 μM), comparable with the commercial herbicide diuron (IC50 = 0.3 μM). The data suggest that this class of compounds interfere at the reducing side of photosystem II, having protein D1 as the most probable target. Molecular docking studies with the plastoquinone binding site of Spinacia oleracea further strengthened this proposal.