24526-69-0

Basic information

• Product Name: 3-CYANO-4-METHYLCOUMARIN
• Synonyms: 4-METHYL-2-OXO-2H-CHROMENE-3-CARBONITRILE;3-CYANO-4-METHYLCOUMARIN;3-CYANO-4-METHYLCOUMARIN 97%;4-methyl-2-oxochromene-3-carbonitrile
• CAS NO: 24526-69-0
• Molecular Formula: C₁₁H₇NO₂
• Molecular Weight: 185.18
• Product Categories: Coumarins;Building Blocks;Heterocyclic Building Blocks
• Mol File: 24526-69-0.mol

Chemical Properties

• Melting Point: 192-195 °C (dec.)(lit.)
• Boiling Point: 352.2°Cat760mmHg
• Flash Point: 168.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.9E-05mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: 3-CYANO-4-METHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-4-METHYLCOUMARIN(24526-69-0)
• EPA Substance Registry System: 3-CYANO-4-METHYLCOUMARIN(24526-69-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 24526-69-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Cyano-4-methylcoumarin is used as a reactant for various organic reactions and the synthesis of organic compounds. Its unique structure and properties make it a valuable component in the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Cyano-4-methylcoumarin is used as a key intermediate in the synthesis of various drugs and drug candidates. Its versatility in organic synthesis allows for the development of new medications with potential therapeutic applications.
Used in Chemical Research:
3-Cyano-4-methylcoumarin is also utilized in chemical research as a model compound for studying various chemical reactions and mechanisms. Its properties and reactivity provide valuable insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, 3-Cyano-4-methylcoumarin may be employed in the development of new materials with specific properties, such as optical, electronic, or mechanical characteristics. Its unique structure and functional groups can be exploited to create novel materials with potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1886, 1953 DOI: 10.1021/ja01104a032

InChI:InChI=1/C11H7NO2/c1-7-8-4-2-3-5-10(8)14-11(13)9(7)6-12/h2-5H,1H3

Upstream product

• 108-24-7 acetic anhydride 
• 118-93-4 o-hydroxyacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 
• 14974-24-4 2,2-difluoro-4-methyl-benzo-1,3,2-2H-dioxaborine 
• 41078-17-5 3-cyano-4-methyl-benzopyran-2-imine 
• 107-91-5 cyanoacetic acid amide 
• 109-77-3 malononitrile 
• 24526-79-2 Cyano-(2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester 

Downstream Products

• 134305-41-2 3-amino-4-cyano-5-(3,4-dioxymethylenephenyl)benzocoumarin 
• 209617-29-8 4(2'-dimethylaminoethenyl)-2-oxo-2H-benzo[b]pyran-3-carbonitrile 

Relevant articles and documents

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New derivatives of 2-oxo-4-vinyl-2H-chromene-3-carbonitrile have been synthesized by the Knoevenagel reaction of 4-methyl-2-oxo-2H-chromene-3-carbonitrile with aromatic and heteroaromatic aldehydes. The first hyperpolarizability β for the obtained compoun

Easy solventless synthesis of new mono and bis amino-5H-chromeno [3,4-c] pyridin-5-one derivatives

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On the Condensation of 2,2-Difluoro-4-methyl-benzo[d]-1,3,2-dioxaborines with Cyano Acetic Acid Derivatives. Formation and Transformation of 3-Cyano-4-methyl-benzo [b]pyran-2-ones and their 2-Imine Precursors

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One-Pot Green Synthesis of 2-Oxo-2H-chromene-3-carbonitriles Using Dual-Frequency Ultrasonication

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Palladium-Catalyzed Regioselective and Diastereoselective C-Glycosylation by Allyl-Allyl Coupling

A Pd-catalyzed C-glycosylation reaction was developed by allyl-allyl coupling process using Achmatowicz rearrangement products as donors and methylcoumarins as acceptors under mild conditions. This method featured regio- and diastereoselectivities, stereo

Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives

The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.

Iridium-catalyzed direct asymmetric vinylogous allylic alkylation

The catalytic asymmetric vinylogous allylic alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

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The in situ formed 4-oxo-4H-thieno[3,4-c]chromene-3-diazonium sulfate (5) in the coupling reactions involving the parent 2-aminothiophene (4) and various phenolic and arylamines’ couplers, readily undergoes homocyclotrimerization at low temperature to aff

Iodine-mediated one-pot synthesis of 3-cyanocoumarins and 3-cyano-4-methylcoumarins

2-Hydroxybenzaldehydes 1a-e on reaction with malononitrile (2) in the presence of iodine as catalyst give 3-cyanocoumarins 3a-e in one step under thermal heating as well as under microwave irradiation. The latter conditions are much more efficient in terms of time (2-5 min) and yield as compared to the thermal conditions (2-2.5 h). Following a similar procedure, 3-cyano-4-methylcoumarins 3f-i were also prepared by the reaction of 2-hydroxyacetophenones 1f-i with 2.