74696-96-1

Basic information

• Product Name: 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE
• Synonyms: 3-Acetyl-7-(diethylamino)-2H-chromen-2-one, 3-Acetyl-7-(diethylamino)-2-oxo-2H-chromene
• CAS NO: 74696-96-1
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.31
• Mol File: 74696-96-1.mol

Chemical Properties

• Melting Point: 150-153 °C
• Boiling Point: 463.1 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: /
• Density: 1.193 g/cm³
• Vapor Pressure: 9.33E-09mmHg at 25°C
• Refractive Index: 1.582
• PKA: 2.82±0.20(Predicted)
• CAS DataBase Reference: 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE(74696-96-1)
• EPA Substance Registry System: 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE(74696-96-1)

Safety Data

• Hazardous Substances Data: 74696-96-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE is used as a potential building block for the development of pharmaceutical products due to its unique chemical structure and heterocyclic characteristics. Its potential applications in this field may include the creation of new drugs or the enhancement of existing ones, although further research is required to determine its specific utility and safety profile.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE is used as a subject of study for understanding the properties and reactivity of chromenones. Its structure and functional groups may provide insights into the synthesis of new compounds or the modification of existing ones, contributing to the advancement of organic chemistry knowledge.
Used in Material Science:
3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE may also be used as a component in the development of new materials, given its aromatic and heterocyclic nature. Its potential applications in material science could include the creation of novel materials with unique properties, such as improved stability, reactivity, or other characteristics that could be beneficial in various industries. However, further investigation is needed to explore these possibilities and assess the safety and practicality of using 3-ACETYL-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE in material development.

InChI:InChI=1/C15H17NO3/c1-4-16(5-2)12-7-6-11-8-13(10(3)17)15(18)19-14(11)9-12/h6-9H,4-5H2,1-3H3

Upstream product

• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 141-97-9 ethyl acetoacetate 
• 20754-01-2 1-ethoxy-2,4-pentanedione 
• 102-01-2 N-phenylacetoacetamide 
• 91-68-9 3-diethylaminophenol 
• 28705-46-6 ethyl 7-diethylaminocoumarin-3-carboxylate 
• 20571-42-0 7-diethylamino-2H-benzopyran-2-one 
• 68-12-2 N,N-dimethyl-formamide 
• 105-53-3 diethyl malonate 
• 105-45-3 acetoacetic acid methyl ester 
• 133590-13-3 3-bromo-7-(diethylamino)-2H-chromen-2-one 
• 1185907-05-4 7-(diethylamino)-3-ethynyl-2H-chromen-2-one 
• 23764-68-3 5-Diethylamino-2-{[(E)-4-nitro-phenylimino]-methyl}-phenol 
• 82222-37-5 (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol 

Downstream Products

• 152208-79-2 7-diethylamino-3-(3-(N-ethyl-N-(2-piperidinoethyl)-4-aminophenyl)propenoyl)coumarin 
• 1366003-75-9 9-diethylamino-5-methyl-3-phenyl-[1]-benzopyrano-[4,3-d]-pyrazolo-[3,4-b]-pyridine-6-one 
• 1131568-01-8 9-diethylamino-1,5-dimethyl-3-phenyl-[1]-benzopyrano-[4,3-d]-pyrazolo-[-3,4-b]-pyridine-6-one 
• 1366003-76-0 9-diethylamino-5-methyl-1,3-diphenyl-[1]-benzopyrano-[4,3-d]-pyrazolo-[3,4-b]-pyridine-6-one 
• 1366003-77-1 9-diethylamino-3,5-dimethyl-1-phenyl-[1]-benzopyrano-[4,3-d]-pyrazolo-[3,4-b]-pyridine-6-one 
• 1415033-20-3 7-methyl-2-phenyl-11-(7-diethylaminocoumarin-3-yl)-3a,10,11,11a-tetrahydro[1]benzopyrano[3,4-e]isoindole-1,3,4-2H-trione 
• 106618-34-2 C₂₂H₂₀ClNO₃ 

Relevant articles and documents

Detection of SO2 derivatives using a new chalco-coumarin derivative in cationic micellar media: Application to real samples

A new probe (E)-7-(diethylamino)-3-(3-(thiophen-2-yl)acryloyl)-2H-chromen-2-one (ChC16) was synthesized and studied as a turn-on fluorescent probe, based on a Michael addition mechanism for sensing SO2 derivatives, which is favored in the presence of cationic micellar media such as cetylpyridinium bromide (CPB). The probe showed high selectivity and sensitivity toward bisulfite over other anions and biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), with a detection limit of 240 nM. Moreover, the probe showed great potential for its practical application in the detection of bisulfite in real samples, such as dry white wine, and in bioimaging.

A multifunctional fluorescent probe for highly selective detection of hydrazine and discovering the interplay between AIE and ICT

A multifunctional luminescent material (BC–B) was synthesized, which exhibits aggregation-induced emission (AIE) enhancement property in high water fraction. The AIE shows a significant impact on the intramolecular charge transfer (ICT) process by control

A Fluorescent coumarinylalkyne probe for the selective detection of mercury(II) ion in water

A coumarin-based alkyne was developed as a fluorescent chemodosimeter for the selective detection of mercuric ion. It showed a high selectivity and sensitivity to mercury(II) ion over other metal ions in water.

Coumarin based hydrazone as an ICT-based fluorescence chemosensor for the detection of Cu2+ ions and the application in HeLa cells

We have constructed a new coumarin based fluorescence probe BENZPYR with ICT character through condensation of N, N-diethylamino-3-acetyl coumarin with 2-hydrazinobenzothiazole. The absorbance and fluorescence spectral characteristics of BENZPYR revealed that the chemosensor can specifically detect for Cu2+ ions over other different metal ions and the lowest limit of detection was found in nano molar range. The turn off sensor of BENZPYR is related to chelation enhanced quenching (CHEQ) and intramolecular charge transfer (ICT) processes were serve as excellent fluorescent detection of Cu2+ ions in DMF medium. Fluorescence microscopy experiments revealed that probe BENZPYR may have application as a fluorophore to detect the Cu2+ in living cells. The simulated DFT analysis of electronic and structural properties and also UV–vis absorption spectra are in well accordance with the experimental UV–vis absorption spectra.

Controlled keto-enol tautomerism of coumarin containing β-ketodithioester by its encapsulation in cucurbit[7]uril

Conventional spectroscopy techniques (UV-Vis, fluorescence and NMR), mass spectrometry and molecular modeling studies are used to assess the inclusion of cucurbit[7]uril (CB7) with coumarin 7-N,N-diethylamino-2H-chromen-2-one derivatives bearing ethyl acetoacetate (CAM1) and methyl β-ketodithioester (CAM2) moieties. For the first time, it has been demonstrated that the macrocycle CB7 is able to stabilize the keto tautomeric form of both coumarin derivatives. More interestingly, it was also seen that for CAM2, the macrocycle CB7 shifts the keto-enol equilibrium from its enol form to the keto tautomer after its inclusion, establishing important differences with inclusion in β-CD, while for CAM1, the macrocycle CB7 maintains the original keto form.

Facile synthesis and fluorescent properties of two novel 4-aryl-2,6-dicoumarinylpyridines

Two novel 4-aryl-2,6-dicoumarinylpyridines were synthesised in the presence of tetrabutylammonium hydrogen sulphate via a one-pot reaction. In addition, the absorption and fluorescence spectra of the synthesised compounds in chloroform were measured for the first time.

A novel coumarin-based pyrazoline fluorescent probe for detection of Fe3+ and its application in cells

A novel coumarin-based pyrazoline fluorescent probe A was synthesized through a four-step reaction. The structure was characterized by 1H NMR(Nuclear magnetic resonance), 13C NMR and HR-ESI-MS(High resolution electrospray ionization mass spectrometry). The optical properties of the fluorescent probe was investigated by UV–vis absorption and fluorescence emission spectra. The results showed that the addition of Fe3+ makes the fluorescence emission spectra of A quenched and displayed a linear fluorescence response to Fe3+ with a detection limit of 1.01 × 10?7 M. It also shows good reversibility upon addition of EDTA(Ethylene diamine tetraacetic acid). The structure of the fluorescent probe was optimized by DFT(Density functional theory) calculations, and the binding mechanism between the fluorescent probe and the recognition ion was explained. Moreover, the probe also has practical application in cell imaging.

Emission behavior of naphthalimide-coumarin cassette

In this contribution, a dye (C8-alkyl substituted Naphthalimide-Coumarin, CNC) with naphthalimide and coumarin incorporated together with -NHN = bridge unit. The compound was fully characterized by NMR and HRMS spectroscopic techniques. Highly emissive character was investigated in detail in various polar environments. The emission maximum varied from 430 to 470?nm. In polycarbonate film, CNC is also highly emissive with 560?nm emission peak. While in sold, the emission maximum was further shifted to 580?nm due to the more tightly packing mode than that in film. The C8-alkyl substitution enhances the solubility of CNC and also contributes most to its solid emission.

A sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to α,β-unsaturated ketones

Compound 1 was designed and synthesized as a new fluorescent thiol probe. Probe 1 was constructed on the basis of the conjugate 1,4-addition of thiols to α,β-unsaturated ketones. Notably, probe 1 has suitable water solubility, which allows the sensing assay to be performed in water. Probe 1 is highly sensitive for thiols with a 211-fold fluorescence dynamic range and a low detection limit of 9.25 × 10-7M. The major features of probe 1 also include a high selectivity for thiols over other relevant biological species, excitation and emission in the visible region, rapid functioning at pH 7.4, and a good linear relationship between the fluorescence signal and the thiol concentration. Accordingly, these desirable characteristics may render probe 1 as potentially useful for biological applications.

Synthesis and fluorescent properties of coumarin–chalcone hybrids

Four coumarin–chalcone hybrids were synthesised utilising condensation of acetylcoumarin with three benzaldehydes and cinnamaldehyde, respectively. Moreover, the absorption and fluorescence spectra of these synthesised compounds in dichloromethane were me