15119-34-3

Basic information

• Product Name: 3-CYANOCOUMARIN
• Synonyms: 2-oxo-2h-1-benzopyran-3-carbonitril;2-oxo-2h-1-benzopyran-3-carbonitrile;RARECHEM AB KA K004;3-CYANOCOUMARIN;Coumarin-3-carbonitrile, 97%;2-oxochromene-3-carbonitrile
• CAS NO: 15119-34-3
• Molecular Formula: C₁₀H₅NO₂
• Molecular Weight: 171.15
• Product Categories: Coumarin;Building Blocks;Coumarins;Heterocyclic Building Blocks
• Mol File: 15119-34-3.mol
• Article Data: 58

Chemical Properties

• Melting Point: 184-188 °C(lit.)
• Boiling Point: 350.7 °C at 760 mmHg
• Flash Point: 167.2 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 4.32E-05mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: 3-CYANOCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANOCOUMARIN(15119-34-3)
• EPA Substance Registry System: 3-CYANOCOUMARIN(15119-34-3)

Safety Data

• WGK Germany: 3
• RTECS: DJ2218100
• Hazardous Substances Data: 15119-34-3(Hazardous Substances Data)

Usage

General Description

3-Cyanocoumarin is a chemical compound with the molecular formula C11H7NO2. It is a derivative of coumarin, a natural occurring compound found in various plants. 3-Cyanocoumarin is commonly used in the production of fluorescent dyes and optical brighteners due to its strong fluorescence properties. It is also used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Additionally, 3-Cyanocoumarin has been studied for its potential applications in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Its unique structural and optical properties make it a versatile compound with numerous potential industrial and research applications.

InChI:InChI=1/C10H5NO2/c11-6-8-5-7-3-1-2-4-9(7)13-10(8)12/h1-5H

Upstream product

• 90-02-8 salicylaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 6968-92-9 2-(2-hydroxybenzylidene)malononitrile 
• 136708-37-7 3-propionyl-2H-1-benzopyran-2-one 
• 140-87-4 Cyanoacetohydrazide 
• 4974-42-9 N-isopropylidenecyanoacetylhydrazine 
• 55819-76-6 2'-acetyl-2-cyanoaceto-hydrazide 
• 89-95-2 2-methyl-benzyl alcohol 
• 109-77-3 malononitrile 
• 3949-36-8 3-acetylcoumarin 
• 100-52-7 benzaldehyde 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 
• 372-09-8 cyanoacetic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 59577-13-8 3-(2-hydroxyphenyl)propanenitrile 
• 2445-82-1 3-methylcoumarine 
• 412338-88-6 (3-Methyl-2-oxo-chroman-4-yl)-acetonitrile 
• 132755-47-6 nitrile of 2,2-dichloro-3-(2-hydroxyphenyl) cyclopropanecarboxylic acid 
• 91-64-5 coumarin 
• 1846-91-9 2-oxo-2H-chromene-3-carbohydrazide 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 30866-42-3 N'-(2-hydroxybenzylidene)-2-oxo-2H-chromene-3-carbohydrazide 
• 13268-54-7 1-tosyl-1, 2-dihydroquinoline 
• 1388215-73-3 1-hydroxy-4-(2-hydroxyphenyl)-2,5-dioxopyrrolidine-3-carbonitrile 

Relevant articles and documents

Facile, efficient, and eco-friendly synthesis of benzo[b] pyran-2-imines over MgO and transformation to the coumarin derivatives

(Chemical Equation Presented) Room temperature synthesis of benzo[b]pyran-2-imine derivatives via the Knoevenagel condensation of malononitrile and cyanoacetates with salicylaldehyde derivatives over MgO and their transformation to the known coumarins is described. The satisfactory results were obtained with good yields, short reaction time, and simplicity in the experimental procedure.

Synthesis and optical properties of coumarins and iminocoumarins: Estimation of ground- and excited-state dipole moments from a solvatochromic shift and theoretical methods

The optical properties of coumarin and iminocoumarin were investigated in different solvents by UV/vis absorption and fluorescence spectroscopy at room temperature (298 K). These compounds were characterized by UV-vis, FT-IR, mass spectroscopy and NMR. A bathochromic shift is observed in absorption and fluorescence spectra of our molecules with increasing solvent polarity. Solvatochromic correlations were used to obtain the ground-state and excited-state dipole moments. The excited-state dipole moments for all the molecules were found to be larger than the corresponding ground-state dipole moments.

Copper(I)-promoted cycloalkylation-peroxidation of unactivated alkenes via sp3 C-H functionalisation

A copper(i)-promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C-O and C-C bonds via sp3 C-H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.

Novel bis(dihydropyrano[3,2-c]chromenes): Synthesis, Antiproliferative Effect and Molecular Docking Simulation

An efficient and convenient route for the synthesis of novel bis dihydropyrano[3,2-c]chromenes is reported. The synthetic pathway involves one-pot, multicomponent reaction of bis-aldehydes, malononitrile, and 4-hydroxycoumarin in the presence of pyridine

Catalyzed preparation of ylidenemalononitriles and 3-cyanocoemarin in water

As sodium hydroxide is used as catalyst, Knoevenagel condensation of malononitrile with aromatic aldehydes can take place at room temperature in water. 3-Cyanocoumarin was obtained by one-pot synthesis.

Transformations of coumarins accompanied by intermediate opening and recyclization of the lactone ring 3. Study of the reactions of 3-ethoxy-carbonylcoumarins with cyanoacetyl-hydrazines by NMR spectroscopy

The reaction of 3-ethoxycarbonylcoumarin with derivatives of cyanoacetylhydrazine directly in the sample tube of the NMR spectrometer was investigated by 1H NMR spectroscopy. The structure of the components of the reaction mixtures was establis

S(RN)1C-arylation of phenols by azosulfides: A novel synthesis of dibenzo[b,d]pyran-6-ones

The ortho-arylation of phenols by (2-cyanoaryl)azo t-butyl (or phenyl) sulfides in S(RN)1 conditions, followed by a silica-gel-catalysed lactonisation of the resulting 2-cyano-2'-hydroxybiphenyls, leads to dibenzo[b,d]pyran-6-ones.

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.