25548-89-4

Basic information

• Product Name: 10-methoxy-10-phenylanthracen-9(10H)-one
• CAS NO: 25548-89-4
• Molecular Formula: C₂₁H₁₆O₂
• Molecular Weight: 300.3505
• Mol File: 25548-89-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 437°C at 760 mmHg
• Flash Point: 188.7°C
• Density: 1.23g/cm³
• Vapor Pressure: 7.74E-08mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: 10-methoxy-10-phenylanthracen-9(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 10-methoxy-10-phenylanthracen-9(10H)-one(25548-89-4)
• EPA Substance Registry System: 10-methoxy-10-phenylanthracen-9(10H)-one(25548-89-4)

Safety Data

• Hazardous Substances Data: 25548-89-4(Hazardous Substances Data)

Usage

Structure

A derivative of anthracene, a polycyclic aromatic hydrocarbon, with a methoxy group and a phenyl group attached to the anthracene ring.

Functional groups

Methoxy (-OCH3) and phenyl (C6H5) groups.

Aromaticity

Due to the presence of the anthracene ring and phenyl group.

Reactivity

Can undergo electrophilic aromatic substitution, nucleophilic aromatic substitution, and other reactions typical of aromatic compounds.

Organic synthesis

Used as a building block in the synthesis of organic molecules.

Pharmaceutical development

Potential applications in the development of pharmaceuticals due to its unique chemical properties and structural characteristics.

Agrochemicals

Potential use in the development of agrochemicals.

Materials science

Potential applications in the development of new materials.

Biological activities

May exhibit interesting biological activities that warrant further investigation.

Solubility

Likely to be soluble in organic solvents such as dichloromethane, ethyl acetate, and acetone, due to its nonpolar nature.

Stability

Relatively stable under normal conditions, but may be sensitive to strong acids, strong bases, and oxidizing agents.

Melting point

Not provided, but expected to be relatively high due to the presence of the rigid anthracene and phenyl groups.

Boiling point

Not provided, but expected to be relatively high due to the large molecular size and the presence of multiple aromatic rings.

Upstream product

• 96179-18-9 10-methoxy-9,10-diphenyl-9,10-dihydro-[9]anthryl hydroperoxide 
• 857596-11-3 (10-chloro-10-phenyl-10H-[9]anthrylidene)-phenyl-amine 
• 95953-44-9 9-Phenyl-10-phenylimino-9,10-dihydro-[9]anthrol 
• 10019-06-4 10-phenylimino-9,10-dihydroanthracen-9-one 
• 13425-08-6 9-methyl-10-phenylanthracene 
• 67-56-1 methanol 
• 5146-30-5 10-phenyl-10-hydroxy-9-anthracenone 
• 855949-45-0 (10-methoxy-10-phenyl-10H-[9]anthrylidene)-phenyl-amine 
• 596-29-2 3,3-diphenyl-2-benzofuran-1(3H)-one 
• 52236-50-7 10-chloro-10-phenyl-anthrone 

Downstream Products

• 136559-06-3 C₂₈H₂₀O₃ 
• 859336-00-8 9-[2]Furyl-10-methoxy-10-phenyl-9,10-dihydro-[9]anthrol 
• 102477-75-8 9-Hydroxy-9-methyl-10-phenyl-9.10-dihydro-anthracen 
• 861082-78-2 9.10-Diphenyl-9.10-dihydro-anthranol-⁽⁹⁾ 
• 860234-09-9 10-Phenyl-9-o-tolyl-9,10-dihydro-[9]anthrol 
• 860728-94-5 10-methoxy-10-phenyl-anthrone-hydrazone 
• 14596-70-4 10-phenylanthrone 
• 13577-28-1 9-phenyl-9,10-dihydroanthracene 

Relevant articles and documents

Thermal rearrangements of di- and triphenyl-substituted benzocyclobutenes and corresponding o-quinodimethanes

7,8-Dimethoxy-7,8-diphenyl- (1c), 7,8-dimethyl-7,8-diphenyl- (1d), 7- methoxy-7,8,8-triphenyl- (1e), 7-methyl-7,8,8-triphenyl- (1f), 7-isocyano- 7,8,8-triphenyl- (1g), and 7,7,8-triphenylbenzocyclobutene (1h) are amenable to a variety of thermal rearrangements following initial electrocyclic ring- opening to the corresponding 7,8-diphenyl- (2c,d) and 7,8,8-triphenyl-o- quinodimethanes (2e-h). meso-1c was found to undergo a facile meso/rac isomerization at room temperature, indicating that other processes such as a symmetry-forbidden disrotatory ring-opening or a stepwise reaction compete with the symmetry-allowed conrotatory process. An estimate of the energy profile of the 1c/2c reaction system was made by kinetic simulation in combination with oxygen trapping of the intermediate o-quinodimethanes (2c) and semiempirical PM3 calculations, and revealed that the barrier for the symmetry-forbidden pathway is merely about 4 kJ · mol-1 higher than that for the symmetry-allowed one. o-Quinodimethanes 2c, 2g, 2e, and 2h underwent further electrocyclic hexatriene-cyclohexadiene ring-closure to give 4a,10- dihydroanthracene derivatives at temperatures between 20 and 80 °C. The 4a,10-dihydroanthracenes were further transformed to 9,10-disubstituted anthracenes by elimination of methanol or HCN, as well as to 9,10-substituted 9,10-dihydroanthracene derivatives. ESR and ENDOR spectroscopic detection of related 9-anthryl radicals lends support to the view that 9,10- dihydroanthracene products are formed by a homolytic hydrogen-transfer reaction (retrodisproportionation). By way of contrast, the aforementioned transformations play only a minor role in the case of methyl-substituted benzocyclobutenes 1d, 1f as here they are overruled by faster 1,5-H shift reactions of the corresponding o-quinodimethanes 2d, 2f, leading to styrene derivatives.