53653-66-0

Basic information

• Product Name: 3-ACETYL-6-CHLORO-2H-CHROMEN-2-ONE
• Synonyms: 3-ACETYL-6-CHLORO-2H-CHROMEN-2-ONE;TIMTEC-BB SBB014381;Nsc73187;3-Acetyl-6-chloro-2H-chromen-2-one, 3-Acetyl-6-chloro-2-oxo-2H-chromene;3-acetyl-6-chloro-2H-1-benzopyran-2-one
• CAS NO: 53653-66-0
• Molecular Formula: C₁₁H₇ClO₃
• Molecular Weight: 222.62
• Mol File: 53653-66-0.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 428.8°Cat760mmHg
• Flash Point: 196.5°C
• Appearance: /
• Density: 1.406g/cm³
• Vapor Pressure: 1.47E-07mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 3-ACETYL-6-CHLORO-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYL-6-CHLORO-2H-CHROMEN-2-ONE(53653-66-0)
• EPA Substance Registry System: 3-ACETYL-6-CHLORO-2H-CHROMEN-2-ONE(53653-66-0)

Safety Data

• Hazardous Substances Data: 53653-66-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7ClO3/c1-6(13)9-5-7-4-8(12)2-3-10(7)15-11(9)14/h2-5H,1H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 635-93-8 5-chlorosalicyclaldehyde 
• 626-34-6 ethyl aminocrotonate 
• 5977-14-0 acetoacetamido 
• 81375-98-6 4,4-bis(ethylsulfanyl)but-3-en-2-one 
• 674-82-8 4-methyleneoxetan-2-one 
• 105-45-3 acetoacetic acid methyl ester 
• 2420-26-0 4-chlorosalicylaldehyde 

Downstream Products

• 106577-99-5 3-(2-bromoacetyl)-6-chloro-2H-chromen-2-one 
• 228854-68-0 propionic acid N'-[4-(6-chloro-2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-hydrazide 
• 106578-09-0 6-Chloro-3-(2-phenyl-thiazol-4-yl)-chromen-2-one 
• 1260653-60-8 C₂₅H₁₆ClFN₄O₂ 
• 326913-97-7 6-chloro-3-[1-(phenylhydrazono)-ethyl]-chromen-2-one 
• 86100-06-3 8-chloro-3-methyl-1-phenyl-1H-chromeno[4,3-c]pyrazol-4-one 
• 1355025-94-3 6-chloro-3-(2-(3-hydroxycarbonyl)phenylamino)acetyl-2H-chromen-2-one 
• 1355026-02-6 6-chloro-3-[2,3-(dihydro-3-(3-hydroxycarbonylphenyl)-2-thioxo-1H-imidazol-5-yl)]-2H-chromen-2-one 
• 38486-12-3 5-chloro-salicylaldehyde azine 
• 1375188-11-6 3-(6-chloro-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 1375188-25-2 5-((3-(6-chloro-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1375188-18-3 5-((3-(6-chloro-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)dihydrothioxopyrimidine-4,6(1H,5H)-dione 
• 1430228-85-5 2-(3-(4-chlorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 
• 1430228-89-9 2-(3-(4-bromophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 

Relevant articles and documents

Microwave-assisted efficient and convenient one-pot synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins under solvent-free conditions

[Figure not available: see fulltext.] An efficient green synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins has been developed. One-pot reaction of 3-acetylcoumarin, malononitrile, and elemental sulfur, catalyzed by L-proline, resulted in the formation of thiophene derivatives, which were used as precursors for the synthesis of 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins. Target compounds were prepared by a one-pot method or stepwise, and NH4OAc was exploited as a reagent and molten salt. Microwave irradiation method was successfully applied to afford the products in excellent yields.

A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity

An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety

Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).