4599-94-4

Basic information

• Product Name: 13H-dibenzo[a,h]fluoren-13-one
• Synonyms: 13H-DIBENZO(A,H)FLUOREN-13-ONE
• CAS NO: 4599-94-4
• Molecular Formula: C₂₁H₁₂O
• Molecular Weight: 280.3194
• Mol File: 4599-94-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 214°C
• Boiling Point: 520.9°C at 760 mmHg
• Flash Point: 233.8°C
• Density: 1.315g/cm³
• Vapor Pressure: 5.98E-11mmHg at 25°C
• Refractive Index: 1.782
• CAS DataBase Reference: 13H-dibenzo[a,h]fluoren-13-one(CAS DataBase Reference)
• NIST Chemistry Reference: 13H-dibenzo[a,h]fluoren-13-one(4599-94-4)
• EPA Substance Registry System: 13H-dibenzo[a,h]fluoren-13-one(4599-94-4)

Safety Data

• Hazardous Substances Data: 4599-94-4(Hazardous Substances Data)

Upstream product

• 879-18-5 naphthalene-1-carbonic acid chloride 
• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 93-09-4 naphthalene-2-carboxylate 
• 612-55-5 2-iodonaphthalene 
• 239-60-1 13H-dibenzo[a,i]fluorene 
• 86854-01-5 13H-dibenzo[ai]fluoren-13-one 
• 53223-75-9 12H-dibenzo[b,h]fluoren-12-one 
• 1314643-17-8 C₂₁H₁₃N 
• 100734-33-6 13-oxo-13H-dibenzo[a,h]fluorene-6-carboxylic acid 
• 6342-87-6 2,3-dihydro-1H-benzindene-1-one 
• 643-79-8 o-phthalic dicarboxaldehyde 

Downstream Products

• 239-85-0 13H-dibenzo[a,h]fluorene 
• 53223-75-9 12H-dibenzo[b,h]fluoren-12-one 

Relevant articles and documents

Reversible Friedel-Crafts acyl rearrangements of planar polycyclic aromatic ketones: Dibenzofluorenones

Dibenzofluorenones undergo reversible Friedel-Crafts acyl rearrangements in PPA at elevated temperatures. The Friedel-Crafts acyl rearrangements of 13H-dibenzo[a,i]fluoren-13-one (DBaiF) yield both 13H-dibenzo[a,h]fluoren-13-one (DBahF) and 12H-dibenzo[b,h]fluoren-12-one (DBbhF). DBahF and DBbhF undergo reversible mutual isomerizations, and their ratio depends on the reaction conditions. The O-protonate DBahFH+ plays a pivotal role in the proposed mechanism of the reversible Friedel-Crafts acyl rearrangements. DBahFH+ may undergo proton migration to give two isomeric σ-complexes: σ-13aH-DBahF+ and σ-12aH-DBahF +, leading, via the respective naphthyl naphthoylium ions βCOβN-βN+ and αCOβN-βN+ to O-protonates DBbhFH+ and DBaiFH+, respectively. The regioselectivity of the rearrangement is expressed by the preferred intramolecular beta-electrophilic attack in βCOβN-βN+ and by the preferred alpha-electrophilic attack in αCOβN-βN +, which indicates a thermodynamic control. The proposed mechanism is supported by the results of the DFT calculations of the dibenzofluorenones, their O-protonates, their σ-complexes and their corresponding naphthyl naphthoylium ions at B3LYP/6-311++G(d,p). DBahF and DBaiF are the kinetically controlled products of the Friedel-Crafts acyl rearrangement, while DBbhF is the thermodynamically controlled product. The aromaticity/antiaromaticity notions in dibenzofluorenones and their O-protonates, estimated by calculated HOMA and NICS indices, are discussed. The Royal Society of Chemistry 2013.

Site-Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

The development of an oriented arylation process dedicated to the naphthalene core is presented. Our approach is based on dual role of N-tosyl carboxamides acting jointly as a directing group in a first C–H arylation step and as a “CO” or “CO–NH” fragment