2107-76-8

Usage

Uses

Used in Pharmaceutical Industry:
5,7-Dihydroxy-4-methylcoumarin is used as an intermediate compound for the synthesis of various pharmaceutical products, specifically pyrano[2,3-h]coumarin derivatives and 5,7-dihydroxy-8-formyl-4-methylcoumarin. These derivatives have potential applications in the development of drugs with specific therapeutic properties.
Used in Chemical Industry:
In the chemical industry, 5,7-Dihydroxy-4-methylcoumarin is used as a starting material for the synthesis of various organic compounds, taking advantage of its unique chemical properties and reactivity.
Used in Research and Development:
5,7-Dihydroxy-4-methylcoumarin is also utilized in research and development settings, where its fluorescence and light-absorbing properties are valuable for studying molecular interactions and developing new methodologies in chemical and biological research.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

5,7-Dihydroxy-4-methylcoumarin is a phenol and lactone. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Lactones react similarly to esters. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Fire Hazard

Flash point data for 5,7-Dihydroxy-4-methylcoumarin are not available. 5,7-Dihydroxy-4-methylcoumarin is probably combustible.

InChI:InChI=1/C10H8O4/c1-5-2-9(13)14-8-4-6(11)3-7(12)10(5)8/h2-4,11-12H,1H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 108-73-6 3,5-dihydroxyphenol 
• 141-97-9 ethyl acetoacetate 
• 75-36-5 acetyl chloride 
• 105-45-3 acetoacetic acid methyl ester 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 67-68-5 dimethyl sulfoxide 
• 66695-25-8 5,7-diacetyloxy-4-methyl-2H-chromen-2-one 
• 4341-76-8 Ethyl 2-butynoate 
• 4525-25-1 Methyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 533-73-3 1,2,4-Trihydroxybenzene 

Downstream Products

• 6093-80-7 5,7-dimethoxy-4-methylcoumarin 
• 111442-53-6 5-hydroxy-4-methyl-7-(toluene-4-sulfonyloxy)-coumarin 
• 69830-33-7 4-methyl-5,7-bis-(toluene-4-sulfonyloxy)-coumarin 
• 7578-55-4 5,7-dimethoxy-4,6-dimethyl-coumarin 
• 350981-82-7 5,7-di-(2'-oxopropyloxy)-4-methylcoumarin 
• 1346896-35-2 C₃₀H₂₄N₂O₄ 
• 1346896-39-6 C₃₀H₂₃NO₅ 
• 1346896-44-3 C₃₀H₂₃NO₅ 
• 1346896-47-6 C₂₄H₁₉NO₅ 
• 1346896-19-2 C₂₄H₂₀N₂O₄ 
• 1346896-23-8 C₃₀H₂₄N₂O₄ 
• 1346896-26-1 C₃₀H₂₃N₃O₆ 

Relevant academic research and scientific papers

Synthesis of coumarin derivatives in a microfluidic flow system employing the Pechmann condensation: A case study

For the synthesis of coumarin derivatives using the Pechmann condensation scheme, an acidic ionic liquid catalyst, abbreviated as [EBsImH][HSO4], was prepared from the ring opening of 1,4-butanesultone by 1-ethylimidazole, followed by the addition of 1 equiv. H2SO4(c). The [EBsImH][HSO4]-catalyzed Pechmann condensation reactions proceeded smoothly in a batch setup, with recyclable [EBsImH][HSO4] showing great catalytic activity. The acidic ionic liquid catalyst [EBsImH][HSO4] was recovered from EtOAc/H2O extraction of the product mixture, where the H2O layer was worked up and dried for reuse in consecutive runs of the Pechmann condensation reactions, maintaining >85% conversion for four times. The catalytic reactions were also carried out in a microfluidic flow setup. The flow parameters, the reactant molar amounts, and the additional H2SO4 as a modifying acid catalyst were optimized in the current case study. A minimum conversion rate of 2.8 g/hr of coumarin derivatives was demonstrated.

CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of coumarins via pechmann reaction in water

The synthesis of coumarins by hydroxyalkylation of phenols with ethyl acetoacetate (via Pechmann reaction) is attempted using magnetically separable and reusable CuFe2O4 nanoparticles in water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

Sulfonated core-shell magnetic nanoparticle (Fe3O4@SiO2@PrSO3H) as a highly active and durable protonic acid catalyst; Synthesis of coumarin derivatives through pechmann reaction

Sulfonic acid supported silica coated magnetic nanoparticles (Fe3O4@SiO2@PrSO3H), was prepared by using low cost precursors and a facile immobilization technique. The final catalyst, which was characterized by XRD, FT-IR, vibrating sample magnetometer (VSM), TEM, and TGA techniques, was found to be an efficient and environmentally benign solid acid for the Pechmann condensation of substituted phenols with ethyl acetoacetate leading to the formation of coumarin derivatives. After the reaction, the catalyst could be effortlessly separated by external magnet and reused for 22 consecutive runs, without any significant loss in catalytic efficiency. The catalytic system presented offers a reusable strategy for the efficient synthesis of coumarin, simplicity in operation, and a green reaction profile by avoiding toxic conventional catalysts and solvents. Green earth and blue sky: Herein, we wish to disclose a simple bench top procedure for the synthesis of sulfonated core-shell magnetic nanoparticles (SMNPs) (Fe3O4@SiO2@PrSO3H) and discuss its performance as a very strong solid acid in the Pechmann condensation reaction.

Meglumine sulfate catalyzed solvent-free one-pot synthesis of coumarins under microwave and thermal conditions

A convenient method has been developed for the Pechmann reaction of phenols and β-keto esters catalyzed by meglumine sulfate. Solvent-free conditions, inexpensive catalyst, short reaction times, high yield, and ease of purification of the products are the advantages of this protocol. This novel catalytic system is expected to contribute to the development of more benign Pechmann condensation reactions of phenols with β-keto esters.

Polyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3); A mild and efficient catalyst for synthesis of 4-metyl coumarins via the Pechmann reaction

Polyvinylpolypyrrolidone-supported boron trifluoride has been studied for synthesis of 4-methyl coumarin by the Pechmann reaction. The reaction proceeded smoothly with hydroxyl phenols and ethyl acetoacetate in good yields in ethanol at reflux conditions. The polyvinylpolypyrrolidone-boron trifluoride complex is a non-corrosive and stable solid catalyst elevated Lewis acid property.

SnCl4 grafted on silica gel: an efficient catalyst for solvent-free synthesis of coumarins via the Pechmann condensation

A facile synthesis of substituted coumarins via Pechmann condensation catalyzed by SnCl4 grafted on silica gel is described, which was conducted under solvent-free condition in high yields. The catalyst is noncorrosive and can be easily prepared and separated from the reaction mixture. This methodology offers some advantages with regard to yield of products, simplicity in operation and green aspects.

The Effects of Exposed Specific Facets and Sulfation on the Surface Acidity of Cu2O Solids

Cuprous oxide microcrystals with {111}, {111}/{100}, and {100} exposed facets were synthesized. 31P MAS NMR using trimethylphosphine as the probe molecule was employed to study the acidic properties of samples. It was found that the total acidic density of samples increases evidently after sulfation compared with the pristine cuprous oxide microcrystals. During sulfation, new {100} facets are formed at the expense of {111} facets and lead to the generation of two Lewis acid sites due to the different binding states of SO4 2? on {111} and {100} facets. Moreover, DFT calculation was used to illustrate the binding models of SO4 2? on {111} and {100} facets. Also, a Pechmann condensation reaction was applied to study the acidic catalytic activity of these samples. It was found that the sulfated {111} facet has better activity due to its higher Lewis acid density compared with the sulfated {100} facet.

Selectfluor: A simple and efficient catalyst for the synthesis of substituted coumarins under solvent-free conditions

Selectfluor is used as an alternative catalyst to conventional catalysts for the synthesis of substituted coumarins via Pechmann condensation of phenols with β-ketoesters under solvent-free conditions at 120 °C. This method of synthesis is simple, cost-effective, requires short reaction time, solvent-free and gives good yields.

Novel traceless liquid-phase synthesis of coumarin derivatives on poly(ethylene glycol) support

Coumarin derivatives were prepared by the von Pechmann reaction of PEG-bound acetoacetate reagent with phenols in the presence of TiCl4 in excellent yield and purity with a facile workup procedure. The polymer reagent could be recycled two to four times without diminishing the yield or purity. Copyright Taylor & Francis Group, LLC.

Photo-cross-linked poly(ether amine) micelles for controlled drug release

In order to improve the stability of micelles and decrease the burst release of loaded drugs, photo-cross-linked micelles were prepared via photodimerization of the coumarin moiety on amphiphilic poly(ether amine) (PEAC). The structures of the obtained monomer and polymers were confirmed by Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV-vis), 1H NMR and 13C NMR (Nuclear Magnetic Resonance, NMR). PEAC could self-assemble into micelles by directly dispersing in water with a hydrophobic coumarin core and a hydrophilic poly(ethylene glycol) (PEG) shell. The photo-cross-linking process of the PEAC micelles was monitored by UV-vis spectroscopy. The morphology and size distribution of the micelles was characterized by transmission electron microscopy (TEM) and dynamic light scattering (DLS). Anticancer drug doxorubicin (DOX) was loaded into the micelles during the process of micelle formation. Photo-cross-linked micelles showed slower drug release and cellular uptake in comparison with the uncross-linked micelles. And both DOX-loaded micelles displayed pH-sensitive release behaviours. Moreover, the DOX-loaded photo-cross-linked micelles exhibit comparative anticancer efficacy as free DOX. These results indicated that photo-cross-linked PEAC micelles can be used as potential drug carriers for intelligent drug delivery.