1194-98-5

Basic information

• Product Name: 2,5-Dihydroxybenzaldehyde
• Synonyms: GENTISALDEHYDE;GENTISIC ALDEHYDE;GENTISINALDEHYDE;5-HYDROXYSALICYLALDEHYDE;2,5-DIHYDROXYBENZALDEHYDE;Benzaldehyde, 2,5-dihydroxy-;2,5-Dihydroxybenzaldehyde, 98+%;2,5-Dihydroxybenzaldchyde
• CAS NO: 1194-98-5
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• EINECS: 214-789-6
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Benzaldehyde;Phenyls & Phenyl-Het;Aromatics
• Mol File: 1194-98-5.mol
• Article Data: 39

Chemical Properties

• Melting Point: 97-99 °C(lit.)
• Boiling Point: 213.5°C (rough estimate)
• Flash Point: 135.1 °C
• Appearance: Yellow to khaki-green/Crystalline Powder
• Density: 1.2667 (rough estimate)
• Vapor Pressure: 0.0029mmHg at 25°C
• Refractive Index: 1.4797 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: 13.8g/l soluble
• PKA: 8.89±0.18(Predicted)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• BRN: 1363961
• CAS DataBase Reference: 2,5-Dihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dihydroxybenzaldehyde(1194-98-5)
• EPA Substance Registry System: 2,5-Dihydroxybenzaldehyde(1194-98-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-37/39-26,37/39-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1194-98-5(Hazardous Substances Data)

Usage

Description

2,5-Dihydroxybenzaldehyde is a building block. It has been used in the synthesis of 2,4-dimethylbenzoylhydrazones with antileishmanial and antioxidant activity.

synthesis

Add 80 mmol of dry paraformaldehyde to a mixture of 12 mmol of the phenol derivative and 2.5 mmol of MgO nanocrystalline (0.1 g). Expose the resulting mixture under microwave irradiation with a power of 650 W. Monitor the progress of the reaction by thin layer chromatography (TLC) developed by n-hexane : ethyl acetate (8 : 2). Add 100 mL of sulfuric acid (15% w/w) to the reaction mixture and heated at 50 °C for 15 min. Cool the reaction mixture to room temperature. Extract the product by dichloromethane (2 x 50 mL). Dry the organic layer over anhydrous magnesium sulphate. Evaporate the solution resulting from filtration to obtain the crude product. Purify the other product by column chromatography using n-hexane : ethyl acetate (95 : 5 to 70 : 30).

Chemical Properties

yellow to khaki-green crystalline powder

Uses

2,5-Dihydroxybenzaldehyde (cas# 1194-98-5) is a compound useful in organic synthesis.

Definition

ChEBI: A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.

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

Upstream product

• 50-00-0 formaldehyd 
• 123-31-9 hydroquinone 
• 67-66-3 chloroform 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 24141-96-6 6,7-dioxabicyclo[3.2.2]nona-3,8-dien-2-one 
• 87905-76-8 2,5-bis(methoxymethoxy)benzaldehyde diethylacetal 
• 87905-77-9 2,5-bis(methoxymethoxy)benzaldehyde 1,3-propanediol acetal 
• 26172-03-2 2-formyl-1,4-benzoquinone 
• 120-12-7 anthracene 
• 100-83-4 meta-hydroxybenzaldehyde 
• 7647-01-0 hydrogenchloride 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 23001-29-8 6-hydroxy spiropyran 
• 90-01-7 salicylic alcohol 

Downstream Products

• 64418-88-8 2-hydroxy-5-acetyloxybenzaldehyde 
• 3524-69-4 2-formyl-1,4-phenylene diacetate 
• 126006-60-8 2-(phenylimino-methyl)-hydroquinone 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 67105-16-2 2-(benzothiazol-4-ylimino-methyl)-benzene-1,4-diol 
• 128943-03-3 3-(2,5-dihydroxybenzylidene)-1,3-dihydroindol-2-one 
• 1084-96-4 2,5-bis(acetyloxy)benzoic acid 
• 105252-90-2 2,5-bis[(4'-(methoxy)benzoyl)oxy]benzaldehyde 
• 13709-07-4 2,5-bis(methoxymethoxy)benzaldehyde 

Relevant articles and documents

Access to functionalized quinones via the aromatic oxidation of phenols bearing an alcohol or olefinic function catalyzed by supported iron phthalocyanine

The controlled oxidation at only one position of compounds with several oxidizable sites, while keeping the other sites intact, has been demonstrated for phenols bearing alcohol or olefinic functional groups. Iron tetrasulfophthalocyanine supported on silica was found to be an efficient catalyst for the preparation of functionalized quinones under mild conditions, with tert-butylhydroperoxide as the oxidant. A novel rapid and mild one-pot procedure for the covalent grafting of iron tetrasulfophthalocyanine onto silica has been developed. The supported catalyst was characterized by chemical analysis, a specific surface study, UV-vis spectroscopy and XPS. A non-radical mechanism for this unusual selective oxidation has been revealed by 18O labelling experiments. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

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CoTPP-CATALYZED REARRANGEMENT OF 1.4-ENDOPEROXIDES

Bicyclic endoperoxides with strained and perturbed diene moiety have been submitted to CoTPP-catalyzed rearrangement.Side reaction, like formation of epoxyenone, has been suppressed and yield of the formation of bisepoxides highly increased.

Preparation method of 2, 5-dihydroxy benzaldehyde

The invention discloses a preparation method of 2, 5-dihydroxy benzaldehyde, which is used for preparing an important intermediate of a liquid crystal compound, and relates to the technical field of liquid crystals. The preparation method comprises the steps of by taking p-methoxyphenol as a raw material, alkyl nitrile as a solvent, paraformaldehyde as a formylation reagent and magnesium chloride and triethylamine as catalysts, reacting for 2-4 hours, extracting reaction liquid by using an organic solvent, washing with water, drying, and evaporating to remove the solvent to obtain liquid 2-hydroxy-5-methoxybenzaldehyde, and then by using toluene as a solvent, and enabling the obtained 2-hydroxy-5-methoxybenzaldehyde to be subjected to a demethylation reaction under the action of anhydrous aluminum trichloride to obtain 2, 5-dihydroxy benzaldehyde; and reacting for 2-4 hours, washing the reaction liquid with water, extracting with an organic solvent, drying, evaporating to remove the solvent, and crystallizing the solvent. The method has the advantages of cheap and easily available raw materials, simple operation and convenient industrial production.

Substrate-Induced Dimerization Assembly of Chiral Macrocycle Catalysts toward Cooperative Asymmetric Catalysis

An artificial system of substrate-induced dimerization assembly of chiral macrocycle catalysts enables a highly cooperative hydrogen-bonding activation network for efficient enantioselective transformation. These macrocycles contain two thiourea and two chiral diamine moieties and dimerize with sulfate to form a sandwich-like assembly. The macrocycles then adopt an extended conformation and reciprocally complement the hydrogen-bonding interaction sites. Inspired by the guest-induced dynamic assembly, these macrocycles catalyze the decarboxylative Mannich reaction of cyclic aldimines containing a sulfamate heading group. The imine substrate can be activated toward nucleophilic attack of β-ketoacid by a cooperative hydrogen-bonding network enabled by sulfamate-induced dimerization assembly of the macrocycle catalysts. Highly efficient (>95 % yield in most cases) and enantioselective (up to 97.5:2.5 er) transformation of a variety of substrates using only 5 mol % macrocycle was achieved.

Preparation method of 2,5-dihydroxybenzaldehyde

The invention provides a method for synthesizing 2,5-dihydroxybenzaldehyde. The method comprises the following steps: with p-dimethoxybenzene as a raw material, carrying out bromination reaction, Grignard reaction and demethylation reaction to obtain the 2,5-dihydroxybenzaldehyde. The preparation conditions are mild, the process is simple, and the industrial application value is high.