72648-43-2

Usage

Type of compound

Polycyclic aromatic hydrocarbon A hydrocarbon compound consisting of multiple aromatic rings, which are closed, unsaturated rings of carbon atoms.

Structure

Four fused benzene rings in a tetrahedral pattern The compound's structure consists of four benzene rings interconnected in a 3D tetrahedral shape.

Substituents

Two carbonyl groups at positions 7 and 12 The compound has two carbonyl groups (C=O) attached to the structure at specific positions, denoted as 7 and 12.

Physical appearance

Yellow-orange crystalline solid The compound's appearance is characterized by a yellow-orange color and a crystalline form.

Research and industrial applications

Building block for synthesis 1,2,3,4-tetrahydrotetraphene-7,12-dione is used as a starting material for creating various organic compounds and materials.

Potential applications

Organic electronics, pharmaceuticals, and advanced technologies The compound has potential uses in the development of electronic devices, new medications, and materials for a range of advanced technologies.

Reactivity and health hazards

High reactivity and potential health risks Due to its high reactivity, the compound may pose health hazards, necessitating careful handling and storage procedures.

Upstream product

• 873377-85-6 1,2,3,4-tetrahydro-12H-benz[a]anthracen-7-one 
• 72648-42-1 (+/-)-7.12-dioxo-(6arH.12acH.12bcH)-1.2.3.4.6.6a.7.12.12a.12b-decahydro-benz[a]anthracene 
• 16434-62-1 1,2,3,4,7,12-hexahydrobenzanthracene 
• 119-64-2 tetralin 
• 105825-02-3 acetic acid-(1,2,3,4-tetrahydro-benz[a]anthracen-7-yl ester) 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 931-49-7 1-ethenylcyclohexene 
• 1940-19-8 1-vinylcyclohexanol 
• 130-15-4 [1,4]naphthoquinone 
• 2622-21-1 1-vinylcyclohexene 
• 78485-95-7 1-Cyclodecyn-5-one 
• 223802-54-8 2,2-dimethoxy-5,6,7,8-tetrahydro-2H-cyclobuta[a]naphthalen-1-one 
• 591-51-5 phenyllithium 
• 63019-33-0 7-methyl-1,2,3,4,7,12-hexahydro-benz[a]anthracene 

Downstream Products

• 72648-44-3 1,2-dihydro-7,12-dimethylbenzanthracene 
• 118658-56-3 C₂₅H₂₀N₂O₄S 
• 72648-41-0 1,2,3,4-tetrahydrobenzanthracen-4,7,12-trione 4-tosylhydrazone 
• 4483-98-1 1,2,3,4-tetrahydrobenz[a]anthracene 

Relevant academic research and scientific papers

Synthesis and Mutagenicity of A-Ring Reduced Analogues of 7,12-Dimethylbenzanthracene

The synthesis and mutagenicity of two derivatives of 7,12-dimethylbenzanthracene (DMBA; 1), i.e., 1,2-H2DMBA (4) and 1,2,3,4-H4DMBA (5), are reported.These analogues (4 and 5) represents dihydro and tetrahydro A-ring reduced forms of DMBA, a region in the parent hydrocarbon (1) proposed to be involved in metabolism to the ultimate carcinogen.The synthesis for 4 without isolation of intermediates from the tosylhydrazone of 1,2,3,4-tetrahydrobenzanthracene-4,7,12-trione (10) by successive reaction with 8 molar equiv of CH3Li, HI, and NaBH4 represents a novel approach to this hydrocarbon now available in sufficient quantity for biological studies.Interestingly, both of these reduced analogues 4 and 5 exhibited mutagenic activity in the Ames assay in the presence or absence of microsomal activation for strains TA98 and TA100.In these strains, DMBA was active only in the presence of S-9 fraction.In the plasmid-deficient strain TA1537, only tetrahydro analogue 5 exhibited mutagenic activity both in the absence and presence of S-9 fraction.

Synthesis of the Angular Ring Tetrahydro Epoxides of the Carcinogens 7- and 12-Methylbenzanthracene and 7,12-Dimethylbenzanthracene

Tetrahydro epoxide derivatives at the 1,2-and 3,4-positions on the angular ring of carcinogens 7- and 12-methylbenzanthracene (7- and 12-MeBA) and 7,12-dimethylbenzanthracene (7,12-DMBA) have been synthesized in order to probe the basis for the tumorigenicity-enhancing effects of methyl groups on polycyclic aromatic hydrocarbons (PAH).The epoxides were prepared from the corresponding dihydro PAH.For the 7-MeBA and 12-MeBA derivatives, access to the dihydro derivatives was achieved by acetoxylation at the 1- and 4-positions of the tetrahydro ring of 7-and 12-acetoxy-1,2,3,4-tetrahydrobenzanthracene, respectively (Scheme II).For the 7,12-DMBA derivatives, oxidation of 1,2,3,4-tetrahydrobenzanthracene-7,12-quinone afforded the 1- and 4-oxo derivatives, which were converted to the respective dihydro compounds (Scheme III).Alkenes 13 and 22, both of which have a 12-methyl group and C1-C2 double bond, were higly susceptible to endoperoxide formation.The dihydro compounds were converted to the epoxides via cyclization of the bromohydrin or bromoacetate derivatives (Scheme IV).The 1,2-bromohydrin and/or bromoacetate derivatives of 3,4-dihydro-12-methylbenzanthracene and 3,4-dihydro-7,12-dimethylbenzanthracene were highly labile and required special handling in order to be purified and converted into the epoxide derivatives.