3018-21-1

Basic information

• Product Name: 1,2-Diphenylcyclobutane
• Synonyms: 1,2-Diphenylcyclobutane;(1S)-1α,2β-Diphenylcyclobutane;1,1'-(Cyclobutane-1α,2β-diyl)bisbenzene;Benzene, 1,1'-(1,2-cyclobutanediyl)bis-
• CAS NO: 3018-21-1
• Molecular Formula: C₁₆H₁₆
• Molecular Weight: 208.3
• Mol File: 3018-21-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 309.1±22.0 °C(Predicted)
• Appearance: /
• Density: 1.044±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2-Diphenylcyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diphenylcyclobutane(3018-21-1)
• EPA Substance Registry System: 1,2-Diphenylcyclobutane(3018-21-1)

Safety Data

• Hazardous Substances Data: 3018-21-1(Hazardous Substances Data)

Usage

General Description

1,2-Diphenylcyclobutane is a chemical compound that consists of two phenyl groups attached to a cyclobutane ring. It is a colorless, crystalline solid with a molecular formula of C18H16. 1,2-Diphenylcyclobutane is mainly used in organic synthesis and as a building block in the production of various pharmaceuticals and fine chemicals. 1,2-Diphenylcyclobutane exhibits interesting stereochemistry and reactivity due to the strain in its cyclobutane ring, making it a valuable tool in the study of organic chemistry. As a result, it is a valuable compound in the development of new chemical reactions and synthetic methods. However, the compound's use is limited due to its high cost and difficulty in synthesis.

Upstream product

• 7694-30-6 cis-1,2-diphenylcyclobutane 
• 3617-23-0 meso-1,4-dichloro-1,4-diphenylbutane 
• 16844-20-5 1,4-dibromo-1,4-diphenyl-butane 
• 67-64-1 acetone 
• 100-42-5 styrene 
• 66090-52-6 3,6-diphenyl-3,4,5,6-tetrahydropyrazine 
• 23808-18-6 3,6-diphenyl-3,4,5,6-tetrahydropyrazine 

Downstream Products

• 100-42-5 styrene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 74-85-1 ethene 
• 3018-20-0 1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 6622-43-1 α,α'-diphenyladipic acid 
• 72887-10-6 1-methoxy-1,4-diphenylbutane 

Relevant articles and documents

Effect of Reaction Media on Photosensitized [2+2]-Cycloaddition of Cinnamates

The outcome of photosensitized [2+2]-cycloaddition reactions of various cinnamates has been compared in different reaction media, including homogeneous organic solutions under inert conditions, degassed water, and aerated physical gels. The reactions were performed under LED blue light (λmax=455 nm) irradiation and [Ir{dF(CF3)ppy}2(dtb-bpy)]PF6 (1.0 mol%) as photocatalyst. The processes were optimized taking into consideration solvent, gelator, and substrate. Comparative kinetics analyses, as well as the effect of the reaction media on the diastereoselectivity of the process, were evaluated during this investigation. In a number of cases, carrying out the reaction in a less polar solvent, like toluene or highly polar solvent, like water had a tremendous impact on the diastereoselectivity of the process, pointing towards an effect on the stabilization of the putative diradical intermediate in this medium. Moreover, while for reactions run in homogeneous solution oxygen needs to be excluded, no erosion in yield is observed when the photoadditions were run in aerated gel media.

Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong π-π-stacking of arene moieties, whereas diastereoselectivity relies on the electronic effects or ortho-substitution of the arene substrate. The utility of this transformation is demonstrated by the formal synthesis of the lignane natural product (±)-Tanegool.

Two-photon generation of the 1,4-diphenyl-1,4-butanediyl biradical: Direct detection and product studies

The 1,4-diphenyl-1,4-butanediyl biradical (3) is generated from 1,4- dichloro-1,4-diphenylbutane (1) or 2,5-diphenylcyclopentanone (8) under several irradiation conditions. The products resulting from this intermediate are styrene (4), 1,2-diphenylcyclobutane (5), and 1-phenyl-1,2,3,4- tetrahydronaphthalene (6). The formation of tetrahydronaphthalenes appears to be a fingerprint for the intermediacy of 1,4-biradicals having a phenyl group attached to one of the radical centers as corroborated in the high-intensity irradiation of 2-phenylcyclopentanone (12). The yield of 6 depends on the substrate and irradiation conditions; this is rationalized as due to a conformational memory effect of the nascent biradical.