230-27-3 Usage
Description
7,8-Benzoquinoline, also known as Benzo[h]quinoline, is a nitrogen-containing polynuclear aromatic hydrocarbon with a dark yellow crystalline solid appearance. It is characterized by its unique chemical structure, which makes it a versatile compound for various applications in different industries.
Uses
Used in Mutagenic Activity Studies:
7,8-Benzoquinoline is used as a starting reagent for studying the mutagenic activities of benzo[f]quinoline, benzo[h]quinolone, and their derivatives in strain TA 100 of Salmonella typhimurium. This application helps in understanding the potential genetic mutations caused by these compounds and their impact on human health.
Used in Environmental Analysis:
In the field of environmental analysis, 7,8-Benzoquinoline is used for the determination of nitrogen-containing polynuclear aromatic hydrocarbons in the gaseous products of the thermal degradation of polymers. The compound is employed in conjunction with high-performance liquid chromatography (HPLC) and fluorescence detection techniques to accurately measure and analyze these harmful substances.
Used in Chemical Synthesis:
7,8-Benzoquinoline serves as a starting reagent for the synthesis of osmium and ruthenium complexes containing an N-heterocyclic carbene ligand. These complexes have potential applications in various fields, including catalysis, materials science, and pharmaceuticals, due to their unique electronic and structural properties.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 7,8-Benzoquinoline could potentially be used in the pharmaceutical industry as a building block for the development of new drugs or as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure and properties make it a promising candidate for drug discovery and development.
?Hazardous Properties
7,8-Benzoquinoline is combustible; burns to produce toxic fumes of nitrogen oxides.
Safety Profile
Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Purification Methods
Purify it as for 3,4-benzoquinoline above. The picrate has m 196o(from Me2CO). [Beilstein 20 H 463, 20 III/IV 4003, 20/8 V 215.]
Check Digit Verification of cas no
The CAS Registry Mumber 230-27-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,3 and 0 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 230-27:
(5*2)+(4*3)+(3*0)+(2*2)+(1*7)=33
33 % 10 = 3
So 230-27-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-14-13(11)12/h1-9H
230-27-3Relevant articles and documents
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Hamada,Takeuchi
, p. 4209 (1977)
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An amine template strategy to construct successive C-C bonds: Synthesis of benzo[: H] quinolines by a deaminative ring contraction cascade
McFadden, Timothy Patrick,Nwachukwu, Chideraa Iheanyi,Roberts, Andrew George
, p. 1379 - 1385 (2022/03/01)
We developed a convergent strategy to build, cyclize and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. Biaryl-linked azepine intermediates can undergo a deaminative ring contraction cascade reaction, excising nitrogen with the formation of an aromatic core. This strategy and deaminative ring contraction reaction are useful for the synthesis of benzo[h]quinolines. This journal is
Merging C-H Vinylation with Switchable 6π-Electrocyclizations for Divergent Heterocycle Synthesis
Hu, Tianhui,Hua, Yuhui,Jiang, Xunjin,Qiu, Huijuan,Shen, Yang,Wu, Yifan,Xiong, Jing,Xu, Beibei,Zeng, Zhixiong,Zhang, Yandong
supporting information, p. 15585 - 15594 (2020/10/20)
Pyridinium-containing polyheterocycles exhibit distinctive biological properties and interesting electrochemical and optical properties and thus are widely used as drugs, functional materials, and photocatalysts. Here, we describe a unified two-step strategy by merging Rh-catalyzed C-H vinylation with two switchable electrocyclizations, including aza-6π-electrocyclization and all-carbon-6π-electrocyclization, for rapid and divergent access to dihydropyridoisoquinoliniums and dihydrobenzoquinolines. Through computation, the high selectivity of aza-electrocyclization in the presence of an appropriate "HCl"source under either thermal conditions or photochemical conditions is shown to result from the favorable kinetics and symmetries of frontier orbitals. We further demonstrated the value of this protocol by the synthesis of several complex pyridinium-containing polyheterocycles, including the two alkaloids berberine and chelerythrine.
Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines
Chen, Shanping,Deng, Guo-Jun,Jiang, Pingyu,Ni, Penghui,Tuo, Xiaolong,Wang, Xiaodong
, p. 8348 - 8351 (2020/03/11)
An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.