2785-98-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2,5-Dimethoxybenzoic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds, such as galbulimima alkaloid GB and 4-dihydrofluoren-2(1H)-ones, for their potential therapeutic applications.
Used in Organic Synthesis:
2,5-Dimethoxybenzoic acid is used as a reagent in organic synthesis for the preparation of different organic compounds through reductive alkylation and other chemical reactions, contributing to the development of new molecules with diverse applications.

InChI:InChI=1/C9H10O4/c1-12-6-3-4-8(13-2)7(5-6)9(10)11/h3-5H,1-2H3,(H,10,11)/p-1

Upstream product

• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 42020-21-3 2,5-dimethoxybenzamide 
• 25245-35-6 1-iodo-2,4-dimethoxybenzene 
• 5312-97-0 2,5-dimethoxybenzonitrile 
• 871889-07-5 3,6-dimethoxy-cyclohexa-2,6-diene-1,2-dicarbonitrile 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 150-78-7 1,4-dimethoxybezene 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 60-29-7 diethyl ether 
• 24599-58-4 2,5-dimethoxy toluene 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 81722-06-7 ethyl 2,5-dimethoxy benzoate 
• 17918-14-8 2,5-dimethoxybenzoyl chloride 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 50472-09-8 3,6-dimethoxy-2-nitrobenzoic acid 
• 89075-18-3 2-(2,5-Dimethoxy-phenyl)-3H-imidazo[4,5-c]pyridine; hydrochloride 
• 22804-57-5 6-Hydroxy-2,2',3,4,5'-pentamethoxybenzophenon 
• 139117-49-0 hexadecyl-1,4-cyclohexanedione 
• 125628-58-2 2,5-Dimethoxy-benzoic acid 4,5-dimethoxy-1-oxo-indan-2-yl ester 
• 129168-54-3 3-Acetoxy-6-hydroxy-2,2',4,5'-tetramethoxybenzophenon 
• 129168-55-4 2,6-bis-(2,5-Dimethoxybenzoyl)-4-acetoxy-3,5-dimethoxyphenol 
• 125628-62-8 2,5-Dimethoxy-benzoic acid 5-methoxy-1-oxo-indan-2-yl ester 
• 101194-82-5 2,5-Dimethoxy-benzoic acid 5,6-dimethoxy-1-oxo-indan-2-yl ester 
• 141957-50-8 Ph₃P=CHC(O)C₆H₃-2,5-(OMe)2 
• 80900-49-8 (3',3'-ethylenedioxypentyl)-2,5-dimethoxy-2,5-cyclohexadiene-1-carboxylic acid 

Relevant academic research and scientific papers

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

Metal single-atom catalysts (SACs) promise great rewards in terms of metal atom efficiency. However, the requirement of particular conditions and supports for their synthesis, together with the need of solvents and additives for catalytic implementation, often precludes their use under industrially viable conditions. Here, we show that palladium single atoms are spontaneously formed after dissolving tiny amounts of palladium salts in neat benzyl alcohols, to catalyze their direct aerobic oxidation to benzoic acids without ligands, additives, or solvents. With this result in hand, the gram-scale preparation and stabilization of Pd SACs within the functional channels of a novel methyl-cysteine-based metal-organic framework (MOF) was accomplished, to give a robust and crystalline solid catalyst fully characterized with the help of single-crystal X-ray diffraction (SCXRD). These results illustrate the advantages of metal speciation in ligand-free homogeneous organic reactions and the translation into solid catalysts for potential industrial implementation.

Aerobic Oxidation of Diverse Primary Alcohols to Carboxylic Acids with a Heterogeneous Pd-Bi-Te/C (PBT/C) Catalyst

Heterogeneous catalytic aerobic oxidation methods represent a near-ideal approach for the conversion of primary alcohols to carboxylic acids. Here, we report that a heterogeneous catalyst composed of Pd, Bi, and Te supported on activated carbon is highly effective for the oxidation of diverse benzylic and aliphatic primary alcohols, including 5-(hydroxymethyl)furfural (HMF) and substrates bearing heterocycles and other important functional groups. In many cases, the desired carboxylic acid product is obtained in >90% yield. Additionally, the catalyst has been demonstrated in a continuous-flow packed-bed reactor for the oxidation of benzyl alcohol, achieving near-quantitative yield while undergoing over 30 000 turnovers.

Catalytic Conversion of Alcohols to Carboxylic Acid Salts and Hydrogen with Alkaline Water

A [RuH(CO)(py-NP)(PPh3)2]Cl (1) catalyst is found to be effective for catalytic transformation of primary alcohols, including amino alcohols, to the corresponding carboxylic acid salts and two molecules of hydrogen with alkaline water. The reaction proceeds via acceptorless dehydrogenation of alcohol, followed by a fast hydroxide/water attack to the metal-bound aldehyde. A pyridyl-type nitrogen in the ligand architecture seems to accelerate the reaction.

ALKYLATION OF PHENOLIC COMPOUNDS

The invention relates to a process for O-alkyiation of a phenolic compound comprising at least two hydroxyl groups bonded to an aromatic hydrocarbon, the process comprising reacting the phenolic compound with an alkylating agent in the presence of a base, at a suitable reaction temperature and for a suitable time period, thereby alkylating the at least two hydroxy] groups. The invention also relates to O-alkylaled phenolic compounds produced by this process.

Photoracemization of Blestriarene C and Its Analogs

Two analogs of blestriarene C (4,4'-dimethoxy-1,1'-biphenanthrene-2,2',7,7'-tetraol) bearing no 7,7'-dihydroxy (3) and 4,4'-dimethoxy groups 4 were prepared. Unlike blestriarene C (1), compounds 3 and 4, as well as 1,1'-biphenanthrene-2,2'-diol (5), do not racemize under fluorescent lamp illumination. Cyclic voltammetry analysis reveals that compound 1 has a lower half-wave potential (E1/2) than compounds 3, 4, 5, suggesting that a redox cycle is involved in the racemization. Compound 1 racemizes by absorbing UV light corresponding to the 1Lb band. During the reaction, no side products are observed. The racemization is significantly inhibited under nitrogen. Based on these observations, we propose a feasible mechanism for the easy racemization of compound 1, which is mediated by a cation radical generated in situ by a reversible photo-induced oxygen oxidation. Chirality 27:479-486, 2015.

Nitromethane in polyphosphoric acid- A new reagent for carboxyamidation and carboxylation of activated aromatic compou

A new method of carboxyamidation of aromatic compounds based on their reaction with nitromethane in polyphosphoric acid has been developed. Upon the hydrolysis of benzamides during the reaction mixture workup, the corresponding benzoic acids can be obtained. Taylor & Francis Group, LLC.

Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 μM, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 ± 0.72 μM, comparable to that of resveratrol, a well-known tyrosinase inhibitor.

BISMUTH MEDIATED OXIDATIONS

The invention relates to a process for the oxidation of a substrate comprising a benzylic alkyl moiety, said process comprising incubating the substrate with a bismuth complex comprising bismuth and a ligand and a stoichiometric source of oxygen.

Efficient and rapid method for the oxidation of electron-rich aromatic aldehydes to carboxylic acids using improved basic hydrogen peroxide

An efficient and rapid method for oxidation of electron-rich aromatic aldehydes to their corresponding carboxylic acids in excellent yields was developed. It is based on the oxidation of methoxy-substituted benzaldehydes in methanol with an improved aqueous basic hydrogen peroxide system. Benzaldehydes with electronwithdrawing substituents are oxidized to the corresponding carboxylic acid in excellent yields under mild reaction conditions. Copyright Taylor & Francis Group, LLC.