24677-78-9

Usage

Uses

Used in Chemical Synthesis:
2,3-Dihydroxybenzaldehyde is used as a key intermediate in the synthesis of various organic compounds, including 2,3-disubstituted benzaldehyde and 2-ethoxy-3-hydroxy-4-nitrobenzoic acid. Its unique chemical structure allows for the creation of a wide range of products with different applications.
Used in Coordination Chemistry:
In coordination chemistry, 2,3-dihydroxybenzaldehyde is used in the synthesis of copper(II) complexes of Schiff bases. These complexes are of interest due to their potential applications in various fields, such as catalysis, magnetism, and pharmacology.
Used in Pharmaceutical Industry:
The electrochemical properties of 2,3-dihydroxybenzaldehyde make it a promising candidate for the development of new drugs and pharmaceutical compounds. Its ability to form complexes with metal ions, such as copper(II), can be exploited to design novel therapeutic agents with improved bioavailability and targeted delivery.
Used in Material Science:
The unique chemical and electrochemical properties of 2,3-dihydroxybenzaldehyde can also be utilized in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. This can lead to advancements in various industries, including electronics, energy, and environmental protection.

Purification Methods

Crystallise the aldehyde from water. [Beilstein 8 III 1979.]

InChI:InChI=1/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H

Upstream product

• 90-02-8 salicylaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 492-88-6 3-ethoxysalicylaldehyde 
• 67-66-3 chloroform 
• 120-80-9 benzene-1,2-diol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 66495-88-3 3-hydroxy-2-methoxybenzaldehyde 
• 218903-24-3 3-isopropoxy-2-methoxybenzaldehyde 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 225793-15-7 phenethyl 2,6-dimethoxyphenyl ether 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 16825-45-9 1-(2,3-dihydroxy-phenyl)-pentadecan-1-ol 
• 86734-60-3 2-(benzyloxy)-3-hydroxybenzaldehyde 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 
• 146559-04-8 N,N'-bis(3-hydroxysalicylidene)ethane-1,2-diamine 
• 141281-43-8 3-(phenyliminomethyl)-1,2-benzenediol 
• 55559-31-4 7-Hydroxybenzisoxazol 
• 126325-43-7 N-(8-hydroxy-2-oxo-2H-chromen-3-yl)benzamide 
• 55477-54-8 3-acetoxy-2-hydroxybenzaldehyde 
• 115142-67-1 3,3'-(3,6,9-trioxaundecane-1,11-diyldioxy)-bis(2-hydroxybenzaldehyde) 
• 132803-42-0 (E)-2-(2-butenyloxy)-3-hydroxybenzaldehyde 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 

Relevant academic research and scientific papers

Synthesis method of drug intermediate 4-bromo-2,3-dihydroxybenzaldehyde

The invention provides a synthetic method of a drug intermediate 4-bromo-2,3-dihydroxybenzaldehyde. According to the method disclosed by the invention, catechol is used as a raw material, and the 4-bromo-2,3-dihydroxybenzaldehyde medical intermediate is successfully synthesized through formylation reaction and bromination reaction under the action of an inorganic base and a phase transfer catalyst. The method has the advantages of high yield, few side reactions, high purity, short synthesis steps, conventional and easily available starting materials, low cost and environmental friendliness, and has a good industrial application prospect.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

Method for fully synthesizing berberine

The invention discloses a method for fully synthesizing berberine, and relates to a drug synthesis method. The method realizes the industrial full synthesis production of the berberine and is made from a bulk organic raw material catechol, the raw material is easily available, and the price is low; 2,3-dimethoxybenzaldehyde is obtained through selective formylation and methylation of the catechol;after a piperonyl ring is obtained through a catechol methylenenation reaction, piperonyl amine is synthesized through a one-step catalytic addition reaction, so that the synthesis steps of the piperonyl amine are shortened, the use of toxic cyanide is avoided, and the process is green and sustainable; condensation hydrogenation and salification reactions adopt a 'one-pot method', and thus the time and the energy are saved, and the cost is decreased. Industrialized full synthesis production of the berberine opens up large-scale production of the berberine, meets the clinical and research needs of the berberine in current anti-tumor, anti-blood pressure, anti-heart rhythm, blood sugar reduction, treatment of Alzheimer's disease and the like, provides effective drugs for reducing pain of patients, and has remarkable economic and social benefits.

Method for preparing 2,3-dihydroxybenzaldehyde by removing methyl of o-vanillin

The invention discloses a method for preparing 2,3-dihydroxybenzaldehyde by removing methyl of o-vanillin. The method comprises the following steps: in an organic solvent, in the presence of aluminumtrichloride and an iodide, the o-vanillin is subjected to an ether bond cleavage reaction at temperature of -20 DEG C to reflux temperature to form the 2,3-dihydroxybenzaldehyde. The method disclosedby the invention has mild conditions, is simple to operate and has a high yield.

A new method for preparing intermediates of Fludioxonil (by machine translation)

The invention relates to the field of organic synthesis, in particular to a new method for preparing intermediates of Fludioxonil. Difluoro [...] formaldehyde intermediate the synthesis method of the cyclization, chlorinated, fluorine exchange, hydrolysis and the like steps to synthesize. The process is complicated, the unit step more, harsh requirements on equipment, and the yield is low, to the detriment of the industrial production. The invention relates to O-vanillin as the starting material, the preparation of 2, 3 - dihydroxy benzaldehyde, with difluorodichloromethane reaction, in the presence of a, cyclization to obtain important [...] formaldehyde intermediate, not only the process is greatly improved, and the yield is high, waste water is less, there are better application value. (by machine translation)

Novel use of amine compounds

The invention provides a preparation method and novel use of amine compounds. Specifically, the invention provides compounds shown in the formula A or their optical isomers, racemes, solvates or pharmaceutically acceptable salts and a medical use thereof. The above compounds can be used for preparation of a pharmaceutical composition or a preparation. The pharmaceutical composition or preparationis used for (a) inhibiting a transient receptor potential channel protein TRPA1 and (b) treating diseases associated with the transient receptor potential channel protein, wherein each group is defined in the specification.

Ether bond cracking method of phenylalkyl ether

The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.