2498-66-0

Basic information

• Product Name: 1,2-BENZANTHRAQUINONE
• Synonyms: tetraphene-7,12(6aH,12aH)-dione;Tetraphene-7,12-dione;6a,12a-dihydrotetraphene-7,12-dione;1,2-Benzo-9,10-anthraquinone;7,12-benz(a)anthraquinone;Benz[a]anthra-7,12-quinone;Benz[a]anthracene-7,12-quinone;Benzanthracene-7,12-dione
• CAS NO: 2498-66-0
• Molecular Formula: C₁₈H₁₀O₂
• Molecular Weight: 258.27
• EINECS: 219-693-8
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 2498-66-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 169-171 °C(lit.)
• Boiling Point: 361.53°C (rough estimate)
• Flash Point: 175.5 °C
• Appearance: yellow to green crystalline powder
• Density: 1.1584 (rough estimate)
• Vapor Pressure: 4.24E-09mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• BRN: 2052941
• CAS DataBase Reference: 1,2-BENZANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZANTHRAQUINONE(2498-66-0)
• EPA Substance Registry System: 1,2-BENZANTHRAQUINONE(2498-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: CW4591000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2498-66-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow to green powder

Uses

Benz[a]anthracene-7,12-dione is a polycyclic aromatic hydrocarbon that is present in the emission soot of biomass fuels combustion. Benz[a]anthracene-7,12-dione is an urban air contaminant and also a potential mutagen & carcinogen.

Synthesis Reference(s)

The Journal of Organic Chemistry, 42, p. 3465, 1977 DOI: 10.1021/jo00442a002

Purification Methods

Crystallise the dione from MeOH (charcoal). toluene, toluene/hexane, Me2CO, or AcOH. Alternatively purify it by sublimation in vacuo, or by zone refining. [Beilstein 7 H 826, 7 I 440, 7 II 760, 7 III 4278, 7 IV 2644.]

InChI:InChI=1/C18H10O2/c19-17-13-7-3-4-8-14(13)18(20)16-12-6-2-1-5-11(12)9-10-15(16)17/h1-10H

Upstream product

• 90-11-9 1-Bromonaphthalene 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 85-44-9 phthalic anhydride 
• 91-20-3 naphthalene 
• 56-55-3 benz[a]anthracene 
• 5343-99-7 1,2-naphthalenedicarboxylic anhydride 
• 100-51-6 benzyl alcohol 
• 73194-63-5 Methyl 1-benzyl-2-naphthoate 
• 205124-18-1 2-(2-ethenylphenyl)-4,4-dimethoxy-3-(2-methyl-1-propenyl)cyclobutenone 
• 590401-48-2 1,4-dimethoxy-3-methyl-2-naphthylboronic acid 
• 39055-47-5 2-bromo-3-methylnaphthohydroquinone 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 3129-39-3 2-bromo-3-methyl-[1,4]naphthoquinone 
• 827347-02-4 2-(1,4-dimethoxy-3-methyl-2-naphthyl)benzaldehyde 

Downstream Products

• 72872-62-9 o,o'-benzil dicarboxylic acid 
• 7475-29-8 9,10-anthraquinone-1,2-dicarboxylic acid 
• 13345-62-5 7-(Chloromethyl)-12-methylbenzanthracene 
• 63020-27-9 ethyl-(12-methyl-benz[a]anthracen-7-ylmethyl)-ether 
• 2518-01-6 7,12-epidioxy-7,12-dihydro-7,12-dimethylbenzanthracene 
• 27018-50-4 7-iodomethyl-12-methylbenz[a]anthracene 
• 111189-58-3 2-(4-benzanthracenyl)cyclohexanone 
• 111189-57-2 2-(4-benzanthracenyl)cyclohexanol 
• 61921-39-9 4-bromo-benz[a]anthracene 
• 57-97-6 7,12-dimethyl-1,2-benzanthracene 
• 80440-44-4 7H-Dibenz[d,e,j]anthracen-7-one 
• 86854-06-0 13H-dibenzanthracen-13-one 
• 60848-01-3 7-Oxo-dibenzanthracen 
• 2518-00-5 7,12-Dihydroxy-7,12-dimethyl-7,12-dihydrobenzanthracen 

Relevant articles and documents

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Catalytic c-c cleavage/alkyne-carbonyl metathesis sequence of cyclobutanones

A ring-opening/alkyne-carbonyl metathesis sequence of alkyne-tethered cyclobutanones catalyzed by AgSbF6 is realized for the first time to furnish multisubstituted naphthyl ketones under mild conditions. A range of substrates decorated with various substituents at different positions were all well accommodated. Preliminary mechanistic studies show that silver salt acted as a Lewis acid to facilitate both C-C cleavage of the cyclobutanone moiety and the subsequent metathesis between C═O and CC bonds.

Photocatalytic degradation of polycyclic aromatic hydrocarbons in GaN:ZnO solid solution-assisted process: Direct hole oxidation mechanism

GaN:ZnO exhibits excellent activity for the photodegradation of PAHs, and the activity can be obviously improved by loading Pt. The degradation of PAHs in the system of GaN:ZnO is induced by the formation of holes. The holes generated then interact with PAHs to produce PAHs+, which is active enough to react with O2.

The synthesis of angularly fused polyaromatic compounds by using a light-assisted, base-mediated cyclization reaction

The synthesis of substituted polyaromatic compounds that contain at least four benzene rings fused together in an angular fashion is described. Suzuki coupling of 1-bromo-3,4-dihydronaphthalene-2-carbaldehyde with a number of aromatic boronic acids affords products such as 1-(1,4-dimethoxy-3-methyl-2-naphthyl)-3,4-dihydronaphthalene-2-carbaldehyde. Exposure of these dihydronaphthalenes to potassium tert-butoxide and DMF at 80°C yields polyaromatic compounds such as 9,14-dimethoxynaphtho[1,2-a]anthracene.