734-88-3

Basic information

• Product Name: ethyl 5,6-benzocoumarin-3-carboxylate
• Synonyms: ethyl 5,6-benzocoumarin-3-carboxylate;5,6-benzocoumarin-3-carboxylic acid ethyl ester;3-Oxo-3H-naphtho[2,1-b]pyran-2-carboxylic acid ethyl ester;ethyl 3-oxo-3H-benzo[f]chromene-2-carboxylate
• CAS NO: 734-88-3
• Molecular Formula: C16H13O4
• Molecular Weight: 269.27202
• EINECS: 211-997-9
• Mol File: 734-88-3.mol
• Article Data: 59

Chemical Properties

• Boiling Point: 359.49°C (rough estimate)
• Flash Point: 247.9°C
• Appearance: /
• Density: 1.2390 (rough estimate)
• Vapor Pressure: 4.06E-09mmHg at 25°C
• Refractive Index: 1.4872 (estimate)
• CAS DataBase Reference: ethyl 5,6-benzocoumarin-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5,6-benzocoumarin-3-carboxylate(734-88-3)
• EPA Substance Registry System: ethyl 5,6-benzocoumarin-3-carboxylate(734-88-3)

Safety Data

• Hazardous Substances Data: 734-88-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O4/c1-2-19-15(17)13-9-12-11-6-4-3-5-10(11)7-8-14(12)20-16(13)18/h3-9H,2H2,1H3

Upstream product

• 135-19-3 β-naphthol 
• 57000-49-4 (5-methoxy-1H-indol-3-yl)acetic acid ethyl ester 
• 105-56-6 ethyl 2-cyanoacetate 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 14103-18-5 ethyl 3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carboxylate 
• 64-17-5 ethanol 
• 71942-38-6 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride 
• 4361-00-6 3-oxo-3H-benzo[f]chromene-2-carboxylic acid 
• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 
• 2033-24-1 cycl-isopropylidene malonate 
• 105-53-3 diethyl malonate 
• 1191-99-7 2,3-dihydro-2H-furan 
• 99988-56-4 methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate 

Downstream Products

• 117665-38-0 N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-3-oxo-3H-benzocoumarin-2-carboxamide 
• 375831-07-5 N-(6-methylpyridin-2-yl)-3-oxo-3H-benzocoumarin-2-carboxamide 
• 330157-43-2 2-[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-3H-benzo[f]chromen-3-one 
• 1329123-07-0 N'-(4-chlorobenzylidene)-3-oxo-3H-benzo[f]chromene-2-carbohydrazide 
• 1329123-05-8 N'-(3-nitrobenzylidene)-3-oxo-3H-benzo[f]chromene-2-carbohydrazide 
• 1329123-04-7 N'-(2-chlorobenzylidene)-3-oxo-3H-benzo[f]chromene-2-carbohydrazide 
• 1329123-03-6 N'-benzylidene-3-oxo-3H-benzo[f]chromene-2-carbohydrazide 
• 134115-88-1 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-3H-benzo[f]chromen-3-one 
• 1329123-06-9 2-[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]-3H-benzo[f]chromen-3-one 
• 314030-41-6 2-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]-3H-benzo[f]chromen-3-one 
• 1329123-08-1 N'-(2-hydroxybenzylidene)-3-oxo-3H-benzo[f]chromene-2-carbohydrazide 
• 64468-29-7 2-(N-Phenylcarboxamido)-3(H)-oxonaphtho<2,1-b>pyran 
• 111488-10-9 C₂₇H₁₉N₃O₅S 
• 111456-27-0 3-(4'-aminophenylsulphonylhydrazinocarbonyl)-5,6-benzocoumarin 

Relevant articles and documents

Development of Novel Imaging Fluorescent Agents Bearing Anti-Inflammatory Drugs: Synthesis, Structural Characterization and Evaluation of Biological Activity

Abstract: A new series of 5,6-benzocoumarin derivatives carrying anti-inflammatory drugs were synthesized via alkylamide spacers, the target to develop novel imaging fluorescent agents as useful technique to cancer early discovery. Experimentally, treatment of N-Boc-1,3-propanediamine with ethyl 5,6-benzocoumarin-3-carboxlate (III) under reflux conditions followed by hydrolyzed with CF3COOH to the corresponding primary amine (V), then treatment of derivative (V) with anti-inflammatory drugs have carboxylic group in presence of DCC (N,N'-dicyclohexylcarbodiimide) as catalyst and MeCN as solvent. The structure of the synthesized compounds was confirmed by FT-IR, NMR (1H,13C) spectral data as well as elemental analysis. The fluorescence properties study was investigated spectrophotometrically in methanol and maximum emission (λem) exhibited within range 411–436 nm, meanwhile, the quantum yields were calculated comparison to Rhodamine 6G as reference. Interestingly, the compound (III) gave a higher quantum yield (ΦF = 0.96), meanwhile, compounds (VII, VIII, IX and XI) gave reasonable quantum yields (ΦF) 0.60, 0.65, 0.78 and 0.84, respectively. All synthesized compounds were screened for their anti-AChE and antimicrobial activity. Based on the results, some of the compounds showed good activity in compared to the standard drugs.

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A two-photon benzocoumarin-NBD dyad for highly selective and sensitive ratiometric detection of H2S in biological samples

Hydrogen sulfide (H2S), the third endogenous gas signaling transmitter, plays an important role in the basic signal conduction process of human physiology and pathology. It is critical to monitor the dynamic change of H2S in living organisms. In this article, a two-photon ratiometric fluorescent probe (BCD) based on the benzocoumarin-NBD framework was first designed and synthesized. The probe showed large emission separation (about 115 nm), excellent selectivity, and high sensitivity. Moreover, it could be applied to ratiometric image endogenous H2S biosynthesis in the living cells and zebrafish.

Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.