Category: 51473-74-6

Optical properties of new fluorescent iminocoumarins. Part 2. Solvatochromic study and comparison with the corresponding coumarin was written by Turki, Hamida;Abid, Souhir;El Gharbi, Rachid;Fery-Forgues, Suzanne. And the article was included in Comptes Rendus Chimie in 2006.Electric Literature of C14H14N2O2 This article mentions the following:

The optical properties of two new iminocoumarin dyes, bearing a cyano group at the 3-position and an N-diethylamino group at the 7-position, were studied by UV-vis absorption and fluorescence spectroscopy in a large number of solvents. Dye 1 bears a free imino group, while dye 2 is substituted by an ethoxycarbonyl group on the imino function. The properties of these dyes were compared with those of 3-cyano-7-diethylaminocoumarin (3). The study shows that the three compounds display close spectroscopic behavior in a large range of solvents, but the iminocoumarins exhibit much better fluorescence efficiency than the coumarin in polar and moderately protic solvents. This shows that iminocoumarin derivatives can advantageously replace coumarins in this type of solvents, and confirms that substitution on the imino group is a convenient way to obtain good fluorescent probes designed for various purposes. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Electric Literature of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Electric Literature of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solid-state fluorescence properties of small iminocoumarin derivatives and their analogues in the coumarin series was written by Abid-Jarraya, Nihel;Khemakhem, Kacem;Turki-Guermazi, Hamida;Abid, Souhir;Saffon, Nathalie;Fery-Forgues, Suzanne. And the article was included in Dyes and Pigments in 2016.Recommanded Product: 51473-74-6 This article mentions the following:

Considering the many potential applications of fluorescent materials, dyes that exhibit emission in the solid state are in high demand, especially if they are easy to prepare and inexpensive. In this respect, exploring the behavior of basic iminocoumarins seemed relevant. The spectroscopic properties of 3-cyano-7-diethylamino-2-iminocoumarin and a derivative bearing an ethoxycarbonyl group were therefore studied in the solid state, and a comparison was made with the corresponding coumarin. The three compounds had very close fluorescence properties in solution In contrast, the coumarin derivative was much more emissive in the solid state than the iminocoumarins. This discrepancy was tentatively related to the crystal packing modes. A comparison was made with 7-diethylaminocoumarin to clarify the role of the cyano group, which may not be advantageous from a spectroscopic viewpoint. Using a solvent-exchange method, the three cyano compounds generated elongated microparticles, the substituted iminocoumarin derivative even led to flat microfibers. This work shows that small coumarins are valuable solid-state fluorescent dyes while small iminocoumarins should be used as building blocks to access more elaborated compounds if solid-state applications are envisaged. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Recommanded Product: 51473-74-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Coumarins: Fast Synthesis by Knoevenagel Condensation under Microwave Irradiation was written by Bogdal, Dariusz. And the article was included in Journal of Chemical Research, Synopses in 1998.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

Condensation of salicylaldehyde or its derivatives with various derivatives of Et acetate in the presence of piperidine led to the synthesis of coumarins by a solvent free reaction under microwave irradiation For example, microwave irradiation of salicylaldehyde with di-Et malonate in the presence of piperidine gave 89% 3-ethoxycarbonylcoumarin. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A study of the relationship between the chemical structures and the fluorescence quantum yields of coumarins, quinoxalinones and benzoxazinones for the development of sensitive fluorescent derivatization reagents was written by Azuma, Kentaro;Suzuki, Sachiko;Uchiyama, Seiichi;Kajiro, Toshi;Santa, Tomofumi;Imai, Kazuhiro. And the article was included in Photochemical & Photobiological Sciences in 2003.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

To develop new fluorescent derivatization reagents, we investigated the relationship between the chem. structures and the fluorescence quantum yields (Φ_f) of coumarins, quinoxalinones and benzoxadinones. Forty-six compounds were synthesized and their fluorescence spectra were measured in n-hexane, Et acetate, methanol and water. The energy levels of these compounds were calculated by combination of the semi-empirical AM1 and INDO/S (CI = all) methods. The ΔE(T_n(n,π*), S₁(π,π*)) (the energy gap between the T_n(n,π*) and S₁(π,π*) states) values were well correlated with the Φ_f values, which enables us to predict the Φ_f values from their chem. structures. Based on this relationship, 3-phenyl-7-N-piperazinoquinoxalin-2(1H)-one (PQ-Pz) and 7-(3-(S)-aminopyrrolidin-1-yl)-3-phenylquinoxalin-2-(1H)-one (PQ-APy) were developed as fluorescent derivatization reagents for carboxylic acids. The derivatives of the carboxylic acids with PQ-Pz and PQ-APy showed large Φ_f values even in polar solvents, suggesting that these reagents are suitable for the microanal. of biol. important carboxylic acids by reversed phase HPLC. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase was written by Paul, Sima;Ghosh, Pritam;Roy, Partha. And the article was included in New Journal of Chemistry in 2020.Reference of 51473-74-6 This article mentions the following:

A coumarin based compound, 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (DCCO), was developed as a visual fluorescent chemodosimeter for selective detection of highly toxic phosgene gas. DCCO exhibits absorption bands at 330 nm and 425 nm. In the presence of phosgene, the absorbance at 330 nm increases and the peak at 425 nm is shifted to 420 nm with decreasing absorbance accompanying a color change from yellow to colorless. The fluorescence intensity of the probe at 483 nm is enhanced in the presence of phosgene (λ_ex = 425 nm) but nerve agents and other acid chlorides including trisphosgene could not induce any significant enhancement of the fluorescence. DCCO on interaction with phosgene is converted to the corresponding nitrile derivative, 7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile (DCC). The quantum yield was increased 13 fold on conversion from DCCO to DCC. The fluorescence enhancement was explained by the ICT mechanism, which was supported by theor. calculations It exhibits a rapid response for naked eye detection of phosgene. DCCO was used for the detection of phosgene in solution and the gas phase. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Reference of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Reference of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

P(RNCH₂CH₂)₃N: an efficient promoter for the synthesis of 3-substituted coumarins was written by Kisanga, Philip;Fei, Xiangshu;Verkade, John. And the article was included in Synthetic Communications in 2002.Synthetic Route of C14H14N2O2 This article mentions the following:

The title compounds wherein R = Me or i-Pr function as efficient promoters for the formation of coumarins in good to excellent yields (80-95%) from salicylaldehydes and di-activated methylene compounds of the type R’CH₂CO₂Et (R’ = CO₂Et, COMe, CN). Although the yields are not generally superior to those reported in the literature, the methodol. applied here is more convenient in that milder conditions and shorter reaction times are facilitated by the use of the aforementioned com. available catalysts. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Synthetic Route of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C14H14N2O2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds was written by Volmajer, Julija;Toplak, Renata;Leban, Ivan;Majcen Le Marechal, Alenka. And the article was included in Tetrahedron in 2005.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The Knoevenagel reaction between 2-hydroxybenzaldehydes and active methylene compounds (malononitrile and Et cyanoacetate) produced iminocoumarins, e.g., I, and/or coumarins. In order to study the reactivity of the prepared iminocoumarins, chlorination and reaction with N-nucleophiles were studied. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly selective chemodosimeter for cyanide based on a doubly activated Michael acceptor type of coumarin thiazole fluorophore was written by Park, Seokan;Kim, Hae-Jo. And the article was included in Sensors and Actuators, B: Chemical in 2012.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

A doubly activated Michael acceptor type of coumarin thiazole fluorophore (1) was prepared and applied for the detection of cyanide ions in aqueous solution The chemodosimeter exhibited a highly selective and sensitive response to cyanide over other various anions through the Michael addition of cyanide to 1. Upon the addition of cyanide ions, the apparent color and fluorescence changes of 1 were observable with a detection limit of 2.3 μM of the cyanide anions in aqueous solution In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts