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

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

Uses

Used in Organic Synthesis:
2,5-Dihydroxybenzaldehyde is used as a key building block in organic synthesis for the creation of a wide range of chemical compounds. Its unique structure allows it to be a versatile component in the formation of various organic molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-Dihydroxybenzaldehyde is used as a starting material for the synthesis of drugs with potential therapeutic applications. Its ability to form 2,4-dimethylbenzoylhydrazones, which have demonstrated antileishmanial and antioxidant activity, highlights its potential in developing treatments for diseases like leishmaniasis and in providing antioxidant therapies.
Used in Chemical Research:
2,5-Dihydroxybenzaldehyde is also utilized in chemical research as a model compound to study various chemical reactions and mechanisms. Its reactivity and structural features make it an ideal candidate for understanding reaction pathways and optimizing synthetic routes in the development of new chemical entities.

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).

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

Upstream product

• 90-02-8 salicylaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 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 
• 113984-70-6 2,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 87905-75-7 2,5-bis(methoxymethoxy)benzaldehyde dimethylacetal 
• 87905-77-9 2,5-bis(methoxymethoxy)benzaldehyde 1,3-propanediol acetal 
• 26172-03-2 2-formyl-1,4-benzoquinone 
• 120-12-7 anthracene 
• 7647-01-0 hydrogenchloride 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 117891-26-6 2,5-dihydroxy-benzaldehyde-selenosemicarbazone 
• 132593-79-4 6-acetoxy-3-(3-methoxy-phenyl)-coumarin 
• 495-08-9 gentisyl alcohol 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 37110-11-5 2,5-dihydroxybenzaldoxime 
• 64418-88-8 2-hydroxy-5-acetyloxybenzaldehyde 
• 3524-69-4 2-formyl-1,4-phenylene diacetate 
• 124061-43-4 N,N'-bis(5-hydroxysalicylidene)ethylene diamine 
• 126006-60-8 2-(phenylimino-methyl)-hydroquinone 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

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.

MgBr2 supported on Fe3O4@SiO2?~?urea nanoparticle: An efficient catalyst for ortho-formylation of phenols and oxidation of benzylic alcohols

Urea was successfully immobilized on the surface of chloropropyl-modified Fe3O4@SiO2 core–shell magnetic nanoparticles, then supported by MgBr2 and acts as a unique catalyst for oxidation of benzylic alcohols to aldehydes and ketones, and ortho-formylation of phenols to salicylaldehydes. The prepared catalyst was characterized by FT-IR, transmission electron microscopy, scanning electron microscopy, X-ray powder diffraction, dispersive X-ray spectroscopy, CHN and TGA. It was found that Fe3O4@SiO2?~?urea/MgBr2 showed higher catalytic activity than homogenous MgBr2, and could be reused several times without significant loss of activity.

Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions

In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.

Platinum(II) complexes with tetradentate schiff bases as ligands: Synthesis, Characterization and detection of DNA interaction by differential pulse voltammetry

Five sterically hindered platinum(II) complexes with tetradentate schiff bases as ligands, [Pt(L)] (L= N,N'-bisalicylidene-1,2-ethylenediamine (L 1), N,N'-bisalicylidene-1,2-cyclohexanediamine (L2), N,N'-bis(5-hydroxylsalicylidene)-1,2-cyclohexanediamine (L3), N,N'-bisalicylidene-1,2-diphenylethylenediamine (L4) and N,N'-bis(3-tert-butyl-5-methyl-salicylidene)-1,2- diphenylethylenediamine (L5) ) have been synthesized and characterized by IR spectroscopy and elemental analysis. The sterical hindrance of antitumor drug candidates potentially makes them less susceptible to deactivation by sulphur containing proteins and helping to overcome resistance mechanisms. The interaction of these metal complexes with fish sperm single-stranded DNA (ssDNA) was studied electrochemically based on the oxidation signals of guanine and adenine. Differential pulse voltammetry was employed to monitor the DNA interaction in solution by using renewable pencil graphite electrode. The results indicate that ligands with different groups can strongly affect the interaction between [Pt(L)] complexes and ssDNA due to sterical hindrances and complex [Pt(L 1)] has the best interaction with DNA among the five complexes.

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.

METHOD FOR PRODUCING 2-HYDRAZINOBENZOTHIAZOLE DERIVATIVE

The present invention provides a novel method for producing a 2-hydrazinobenzothiazole derivative. The present invention also provides a method for producing a compound by using the 2-hydrazinobenzothiazole derivative obtained by the production method, and a composition that contains the compound. The present invention also provides a polymerizable composition that is useful in producing film-shaped polymers and contains the compound obtained by the production method. The invention of the present application provides a method for producing a compound represented by general formula (I-C), the method including a step of reacting a compound represented by general formula (I-B) with a compound represented by general formula (I-A) in the presence of at least one compound selected from the group consisting of metal amides, metal hydrides, metal alkoxides, and organic alkali metals. A compound derived from the compound produced by the production method, and a composition that contains the compound are also provided.

Bisketene Equivalents as Diels-Alder Dienes

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.

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.

METHOD FOR PRODUCING ESTER GROUP-CONTAINING COMPOUND

The present invention provides a novel method for producing an ester group-containing compound and a derivative produced using the compound as a synthetic intermediate. The invention also provides a polymerizable composition containing the compound obtained by the production method and a film-shaped polymer obtained by polymerizing the polymerizable composition. The present invention is a method for producing an ester group-containing compound, the method including a mixing step of mixing a condensing agent, a Bronsted acid, a carboxylic acid, and a phenol or an alcohol to prepare a reaction mixture. The Bronsted acid selected is other than the condensing agent, the carboxylic acid, and the phenol.