24677-78-9

Basic information

• Product Name: 2,3-Dihydroxybenzaldehyde
• Synonyms: 2,3-DIHYDROXYBENZALDEHYDE;TIMTEC-BB SBB004190;5,6-Dihydroxybenzaldehyde;Benzaldehyde, 2,3-dihydroxy-;o-Pyrocatechualdehyde;2,3-Dihydroxybenealdehyde;2,3-DIHYDROXYBENZALDEHYDE 99%;3-Formyl-1,2-benzenediol
• CAS NO: 24677-78-9
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• EINECS: 246-398-1
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C7;Carbonyl Compounds;Aromatics;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 24677-78-9.mol
• Article Data: 31

Chemical Properties

• Melting Point: 104-108 °C(lit.)
• Boiling Point: 120 °C / 16mmHg
• Flash Point: 113.2 °C
• Appearance: Light yellow to beige-greenish/Crystalline Powder
• Density: 1,542g/cm
• Vapor Pressure: 0.0252mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 95% ethanol: soluble50mg/mL, clear, colorless to greenish-yellow
• PKA: 8.01±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 2041781
• CAS DataBase Reference: 2,3-Dihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydroxybenzaldehyde(24677-78-9)
• EPA Substance Registry System: 2,3-Dihydroxybenzaldehyde(24677-78-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 24677-78-9(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to beige-greenish cryst. powder

Uses

Different sources of media describe the Uses of 24677-78-9 differently. You can refer to the following data:
1. 2,3-disubstituted benzaldehyde.
2. 2,3-Dihydroxybenzaldehyde was used in the synthesis of copper(II) complexes of Schiff bases. It was also used in the synthesis of 2-ethoxy-3-hydroxy-4-nitrobenzoic acid.

General Description

Electrochemical oxidation of 2,3-dihydroxybenzaldehyde in methanol at various pH has been studied using cyclic voltammetry and controlled-potential coulometry.

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

• 492-88-6 3-ethoxysalicylaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 66495-88-3 3-hydroxy-2-methoxybenzaldehyde 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 10035-10-6 hydrogen bromide 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 64-19-7 acetic acid 
• 100-83-4 meta-hydroxybenzaldehyde 
• 110-89-4 piperidine 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 67-66-3 chloroform 
• 120-80-9 benzene-1,2-diol 
• 90-02-8 salicylaldehyde 
• 50-00-0 formaldehyd 

Downstream Products

• 126325-43-7 N-(8-hydroxy-2-oxo-2H-chromen-3-yl)benzamide 
• 55477-54-8 3-acetoxy-2-hydroxybenzaldehyde 
• 146559-08-2 N,N',N''-tri(2,3-dihydroxybenzylidene)-2,2',2''-triaminotriethylamine 
• 40739-73-9 2-nitro-7-hydroxybenzofuran 
• 486-79-3 2,3-diacetoxybenzoic acid 
• 86734-60-3 2-(benzyloxy)-3-hydroxybenzaldehyde 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 
• 86734-59-0 3-benzyloxy-2-hydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 168915-08-0 3-(2-chlorophenyliminomethyl)-1,2-benzenediol 
• 141233-06-9 N(CH₂CH₂NCHC₆H₃(OH)2)3 
• 224950-42-9 C₂₅H₂₂O₇ 
• 67985-75-5 2,3-diacetoxybenzaldehyde 

Relevant articles and documents

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.

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.

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.