32277-35-3

Usage

Uses

Used in Organic Synthesis:
1,2-dihydrocyclobuta[a]naphthalene is utilized as a key intermediate in the synthesis of complex organic molecules, leveraging its unique reactivity to form new chemical bonds and structures. Its strained nature allows for the generation of novel compounds with potential applications across various fields.
Used in Materials Science:
In the field of materials science, 1,2-dihydrocyclobuta[a]naphthalene is employed as a component in the development of advanced materials. Its incorporation can lead to the creation of materials with enhanced properties, such as improved stability or unique electronic characteristics, which can be beneficial for various applications.
Used in Pharmaceutical Chemistry:
1,2-dihydrocyclobuta[a]naphthalene is used as a building block in the design and synthesis of new pharmaceutical compounds. Its distinctive structure may contribute to the development of innovative drugs with improved efficacy and selectivity, offering potential therapeutic benefits in the treatment of various diseases.
Used in Chemical Research:
As a model system for understanding the behavior of highly strained organic molecules, 1,2-dihydrocyclobuta[a]naphthalene is instrumental in advancing chemical knowledge. Its study aids in the exploration of new reaction mechanisms, the development of novel synthetic strategies, and the discovery of unexpected chemical properties.

InChI:InChI=1/C12H10/c1-2-4-11-9(3-1)5-6-10-7-8-12(10)11/h1-6H,7-8H2

Upstream product

• 6626-23-9 1-chloromethyl-2-methyl-naphthalene 
• 118-92-3 anthranilic acid 
• 65957-26-8 1,4-Dihydronaphthocyclobuten 

Downstream Products

• 53-70-3 dibenzo[a,h]anthracene 
• 224-41-9 dibenz[a,j]anthracene 

Relevant academic research and scientific papers

1,2-butene and second hydrogen cyclo [α] naphtalenes new synthetic method

The invention discloses a novel synthetic method of 1,2-dihydro cyclobutene [alpha] naphthalene, which comprises the following steps that (1) 2-methylnaphthalene, paraformaldehyde, glacial acetic acid and hydrochloric acid are directly fed; heating and reaction are performed at 60-70 DEG C; a 1-chloromethane-2-methylnaphthalene crude product is prepared; (2) the obtained 1-chloromethane-2-methylnaphthalene crude product is subjected to reduced pressure distillation; unconverted 2-methylnaphthalene is removed; high-purity 1-chloromethane-2-methylnaphthalene is obtained; (3) high-purity 1-chloromethane-2-methylnaphthalene is added to a pyrolyzer for pyrolysis; a 1,2-dihydro cyclobutene [alpha] naphthalene crude product is obtained; and (4) the 1,2-dihydro cyclobutene [alpha] naphthalene crude product is dried, distilled, subjected to column chromatography and condensed; and a target product is obtained. Compared with the prior art, the method takes 2-methylnaphthalene as a basic raw material to prepare 1,2-dihydro cyclobutene [alpha] naphthalene by chloromethylation and pyrolysis cyclization, and is mild in synthetic condition, high in yield, very high in production value and good in industrial prospect.

Aromatization of 1,4-Dihydrobenzocycloalkenes, 1,4-Dihydronaphthocycloalkenes, and Related Systems

A series of methyl-substituted 1,4-dihydrobenzenes has been prepared, and the rates of oxidation of these molecules by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) have been measured.Existing evidence points to the involvement of a positively charged intermediate which is formed as an ion pair in an initial rate-limiting hydride transfer to DDQ.Series of cycloalkyl-fused 1,4-dihydrobenzenes and 1,4-dihydronaphthalines (fused 1,2 and 2,3) have been prepared and the rates of their DDQ induced aromatization have been studied.The results are explained on the basis of inductive effects associated with the size of the fused ringand exocyclic vs. endocyclic bond order preferences.