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
• Article Data: 20

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

4-Methyl-2-oxo-2H-chromene-3-carbonitrile is a useful reactant for various organic reaction and synthesis of organic compounds.

Synthesis Reference(s)

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

General Description

3-Cyano-4-methylcoumarin is a 3-substituted 4-methylcoumarin derivative. Its structural properties, vibrational frequencies and electronic spectra has been studied by density functional theory (DFT). It has been reported to be formed during the Knoevenagel condensation of o-hydroxyacetophenone with ethyl cyanoacetate catalyzed by calcined Mg-Al hydrotalcite. Synthesis of 3-cyano-4-methylcoumarin, via condensation of o-hydroxyacetophenone with ethyl cyanoacetate in the presence of sodium ethylate, has been reported.

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

• 118-93-4 o-hydroxyacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 109-77-3 malononitrile 
• 107-91-5 cyanoacetic acid amide 
• 108-24-7 acetic anhydride 
• 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 
• 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 
• 607-71-6 4-methyl-2H-chromen-2-one 

Relevant articles and documents

Synthesis and optical properties of new 2-oxo-4-vinyl-2H-chromene-3-carbonitrile dyes

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

A new series of mono and bis amino-5H-chromeno [3,4-c] pyridin-5-one derivatives were prepared via the reaction of primary amines with 4-(2-(dimethylamino)vinyl)-2-oxo-2H-chromene-3-carbonitrile 3. The X-rays structures of 4-(hexylamino)-5H-chromeno[3.4-c

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

By condensation of 2,2-difluoro-4-methyl-benzo[d]-1,3,2-2H-dioxaborines(12) with cyano acetic acid derivatives in presence of weak bases, 3-cyano-4-methyl-benzo[b]pyran-2-ones (13) or their 3-cyano-4-methyl-benzo[b]pyran-2-imine precursors (14) are available in satisfactory yields.

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

Abstract: A green synthesis of 2-oxo-2H-chromene-3-carbonitriles has been carried out in one step by reacting 2-hydroxybenzaldehydes or 2-hydroxyacetophenones with ethyl cyanoacetate under dual-frequency ultrasonica-tion (ultrasonic bath of 40 KHz and probe of 20 KHz). The compounds were obtained in very high yield, and their structures were confirmed by IR and NMR data.

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.