2005-10-9

Basic information

• Product Name: 6H-dibenzo-(b,d)-pyran-6-one
• Synonyms: 6H-dibenzo-(b,d)-pyran-6-one;2'-Hydroxybiphenyl-2-carboxylic acid lactone;3,4-[1,3]Butadieno-2H-1-benzopyran-2-one;6H-benzo[c]chroMen-6-one
• CAS NO: 2005-10-9
• Molecular Formula: C₁₃H₈O₂
• Molecular Weight: 196.21
• Mol File: 2005-10-9.mol
• Article Data: 136

Chemical Properties

• Boiling Point: 354.7°C at 760 mmHg
• Flash Point: 148°C
• Appearance: /
• Density: 1.277g/cm³
• Vapor Pressure: 3.3E-05mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6H-dibenzo-(b,d)-pyran-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-dibenzo-(b,d)-pyran-6-one(2005-10-9)
• EPA Substance Registry System: 6H-dibenzo-(b,d)-pyran-6-one(2005-10-9)

Safety Data

• Hazardous Substances Data: 2005-10-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 5369, 1966 DOI: 10.1021/ja00974a089

InChI:InChI=1/C13H8O2/c14-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)15-13/h1-8H

Upstream product

• 229-95-8 6H-benzo[c]chromene 
• 486-25-9 9-fluorenone 
• 119-36-8 methyl salicylate 
• 947-84-2 2-Biphenylcarboxylic acid 
• 94-36-0 dibenzoyl peroxide 
• 2510-71-6 cis-9,10-dihydroxy-9,10-dihydrophenanthrene 
• 7664-93-9 sulfuric acid 
• 108-24-7 acetic anhydride 
• 119621-87-3 fluorene-9,9-diyl dihydroperoxide; compound with fluoren-9-one 
• 64-19-7 acetic acid 
• 74-88-4 methyl iodide 
• 610-96-8 methyl chlorobenzoate 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 

Downstream Products

• 101880-02-8 2-phenylazo-benzo[c]chromen-6-one 
• 6623-66-1 6-nitro-3,4-benzocoumarin 
• 182355-34-6 2'-Benzyloxy-biphenyl-2-carboxylic acid benzyl ester 
• 51640-90-5 4-Nitro-6H-dibenzo[b,d]pyran-6-one 
• 83358-35-4 6-phenyl-6H-benzo[c]chromen-6-ol 
• 132-64-9 dibenzofuran 
• 119-61-9 benzophenone 
• 17294-89-2 2'-nitro-biphenyl-2-carboxylic acid 
• 18211-41-1 4'-nitro-[1,1'-biphenyl]-2-carboxylic acid 
• 77764-74-0 2'-ethoxybiphenyl-2-carboxylic acid 

Relevant articles and documents

A metal-free oxidation of benzo[c]chromen to benzo[c]chromen-6-ones by t-butyl hydroperoxide in the presence of potassium iodide

An effective and eco-friendly oxidation method for the synthesis of benzo[c]chromen-6-ones is described. The condition constitutes 6 molar ratio TBHP, catalytic KI and pyridine in acetonitrile as the solvent. Altogether, 16 structurally diverse substituted benzo[c]chromen-6-ones were prepared through this protocol from corresponding benzo[c]chromenes in excellent yields. The Japan Institute of Heterocyclic Chemistry.

Efficient one-pot synthesis of dibenzopyranones via a decarboxylative cross-coupling and lactonization sequence

A highly selective palladium bis(acetoacetonate)/copper(I) chloride [Pd(acac)2/CuCl] catalytic system for the preparation of dibenzopyranones has been developed. Tandem decarboxylative coupling and lactonization can be realized in one pot using commercially available starting materials. The reaction proceeded well for a range of different substrates. Copyright

Palladium-catalyzed one-pot Suzuki-Miyaura cross coupling followed by oxidative lactonization: A novel and efficient route for the one-pot synthesis of benzo[c]chromene-6-ones

A number of 6H-benzo[c]chromene-6-ones, 5H-naphtho[1,2-c]chrome-5-ones, and 6H-naphtho[2,1-c]chromene-6-one have been synthesized starting with 2-hydroxyphenylboronic acid and o-bromobenzaldehyde or o-bromonaphthalene carboxaldehyde derivatives via a one-pot Suzuki-Miyaura cross coupling followed by oxidative lactonization reactions. The overall transformation consists of three reactions: Suzuki-Miyaura cross coupling, hemi-acetal formation, and oxidation.

Intramolecular Aromatic C-H Acyloxylation Enabled by Iron Photocatalysis

A mild and efficient protocol for the intramolecular aromatic C-H oxygenation of 2-biphenylcarboxylic acids has been achieved via iron photocatalysis. The 2-biphenylcarboxylic acids with a diverse array of substituents at both phenyl rings could furnish the oxygenation products in good to excellent yields. We speculate that the aryl carboxylate-iron(III) complexes should generate the aroyloxy radicals and iron(II) upon visible light irradiation.

Synthesis of unstable cyclic peroxides for chemiluminescence studies

Cyclic four-membered ring peroxides are important high-energy intermediates in a variety of chemi and bioluminescence transformations. Specifically, a-peroxylactones (1,2-dioxetanones) have been considered as model systems for efficient firefly bioluminescence. However, the preparation of such highly unstable compounds is extremely difficult and, therefore, only few research groups have been able to study the properties of these substances. In this study, the synthesis, purification and characterization of three 1,2-dioxetanones are reported and a detailed procedure for the known synthesis of diphenoyl peroxide, another important model compound for the chemical generation of electronically excited states, is provided. For most of these peroxides, the complete spectroscopic characterization is reported here for the first time.

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THE GENERATION AND PHOTOCHEMISTRY OF INDENONE O-OXIDE AND FLUORENONE O-OXIDE IN LOW TEMPERATURE MATRICES

The photolysis of diazoindene and diazofluorene at 12 K in N2 matrices containing O2 has been studied, using i.r. spectroscopy.The carbonyl oxides, indenone O-oxide and fluorenone O-oxide, were formed by the reaction of O2 with the corresponding carbenes, and under appropriate conditions could be detected as very photolabile species.Photolysis of indenone O-oxide gave indenone and isocoumarin; similar photolysis of fluorenone O-oxide gave fluorenone and dibenzopyran-6-one.

Rh(iii)-catalyzed oxidative C-H bond arylation with hydroquinones: Sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones

An efficient Rh(iii)-catalyzed C-H bond arylation with phenol derivatives was developed for the direct and sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones. This reaction shows good substrate scope and excellent fun

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Free radical reactions for heterocycle synthesis. Part 4: A double ipso substitution reaction for azacoumarins

A highly efficient route to azacoumarins with an unusual mechanism of double ipso substitutions is described.

Generation of benzyne from benzoic acid using C-H activation

ortho C-H activation of benzoic acids with Pd(ii) generates an oxapalladacycle that can decarboxylate to produce a palladium-associated aryne. The arynes then undergo [2+2+2] trimerisation to afford triphenylenes.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

Pseudocyclic bis-N-heterocycle-stabilized iodanes - synthesis, characterization and applications

Bis-N-heterocycle-stabilized λ3-iodanes (BNHIs) based on azoles are introduced as novel structural motifs in hypervalent iodine chemistry. A performance test in a variety of benchmark reactions including sulfoxidations and phenol dearomatizations revealed a bis-N-bound pyrazole substituted BNHI as the most reactive derivative. Its solid-state structure was characterizedviaX-ray analysis implying strong intramolecular interactions between the pyrazole nitrogen atoms and the hypervalent iodine centre.