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

Description

1,2-Benzanthraquinone, also known as Benz[a]anthracene-7,12-dione, is a polycyclic aromatic hydrocarbon (PAH) characterized by its yellow to green powder appearance. It is a compound that can be found in the emission soot resulting from the combustion of biomass fuels, making it an urban air contaminant. Additionally, it is recognized as a potential mutagen and carcinogen due to its harmful effects on human health.

Uses

Used in Environmental Monitoring and Research:
1,2-Benzanthraquinone is used as a marker for [identifying the presence of air pollution] in [urban areas affected by biomass fuel combustion]. Its detection in the environment helps to assess the level of air pollution and the potential health risks associated with it.
Used in Toxicology Studies:
1,2-Benzanthraquinone is used as a research compound for [studying its mutagenic and carcinogenic properties] in [laboratory settings]. Understanding its effects on biological systems can contribute to the development of strategies for mitigating its harmful impacts on human health and the environment.
Used in Air Quality Regulation and Policy Making:
1,2-Benzanthraquinone is used as a reference substance for [establishing air quality standards and regulations] in [urban areas with significant biomass fuel usage]. Its inclusion in these guidelines aids in the implementation of measures to reduce air pollution and protect public health.

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

• 109589-22-2 2a,3,10,10a-tetrahydro-3,10-etheno-cyclobut[b]anthracene-4,9-dione 
• 85-44-9 phthalic anhydride 
• 91-20-3 naphthalene 
• 64-19-7 acetic acid 
• 590401-48-2 1,4-dimethoxy-3-methyl-2-naphthylboronic acid 
• 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 
• 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

• 27018-50-4 7-iodomethyl-12-methylbenz[a]anthracene 
• 17513-43-8 7-Methyl-7-hydroxy-benzanthron 
• 2518-00-5 7,12-Dihydroxy-7,12-dimethyl-7,12-dihydrobenzanthracen 
• 80440-44-4 7H-Dibenz[d,e,j]anthracen-7-one 
• 86854-06-0 13H-dibenzanthracen-13-one 
• 57-97-6 7,12-dimethyl-1,2-benzanthracene 
• 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 
• 63019-29-4 ethyl-benz[a]anthracen-7-ylmethyl ether 
• 17526-24-8 acetic acid benz[a]anthracen-7-ylmethyl ester 
• 16110-13-7 7-hydroxy-methyl-12-benz[a]anthracene 
• 32766-73-7 7,12-Diphenyl-benzoanthracen 
• 316-49-4 4-methylbenz[a]anthracene 

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.