5628-11-5

Basic information

• Product Name: 4-hydroxy-[2,2]-paracyclophane
• Synonyms: 4-hydroxy-[2,2]-paracyclophane
• CAS NO: 5628-11-5
• Molecular Weight: 224.302
• Mol File: 5628-11-5.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 4-hydroxy-[2,2]-paracyclophane(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-[2,2]-paracyclophane(5628-11-5)
• EPA Substance Registry System: 4-hydroxy-[2,2]-paracyclophane(5628-11-5)

Safety Data

• Hazardous Substances Data: 5628-11-5(Hazardous Substances Data)

Upstream product

• 123439-12-3 4-amino[2.2]paracyclophane 
• 64-19-7 acetic acid 
• 1908-61-8 4-bromo[2.2]paracyclophane 
• 36325-27-6 4-formyl[2.2]paracyclophane 
• 1633-22-3 [2.2]Paracyclophan 
• 196316-30-0 4,16-dibromo[2.2]paracyclophane 
• 24262-20-2 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol 
• 5628-13-7 (+/-)-4-acetoxy[2.2]paracyclophane 
• 5551-40-6 5-Hydroxy-4-methylmercypto-<2,2>paracyclophan 

Downstream Products

• 5628-16-0 <2.2>paracyclophane-4,7-dione 
• 82886-83-7 <2.2>paracyclophane-4,5-quinone 
• 313048-26-9 rac-4-benzoyl-5-hydroxy[2.2]paracyclophane 
• 865164-05-2 5-(p-bromobenzoyl)-4-hydroxy[2.2]paracyclophane 
• 157018-15-0 (R_p)-(+)-4-hydroxy-[2.2]paracyclophane 
• 157018-15-0 (S_p)-4-hydroxy-[2.2]paracyclophane 

Relevant articles and documents

3D Coumarin Systems Based on [2.2]Paracyclophane: Synthesis, Spectroscopic Characterization, and Chiroptical Properties

In this article, we report the preparation of a series of [2.2]paracyclophane-fused coumarin systems through a simple and general procedure involving a transition-metal-catalyzed cyclization of aryl alkynoates as the key step. We also highlight the influence of the [2.2]paracyclophane (pCp) motif and its "phane" interactions on the spectroscopic properties of the newly synthesized fluorophores, which emit in the blue-green region of the visible spectrum (?em up to 560 nm) and show extremely large Stokes shifts (up to 230 nm). Finally, we demonstrate that our straightforward approach can easily be used to access optically active planar chiral 3D coumarins. Compared to previously described fluorescent paracyclophanes and other organic dyes, our compact heteroaromatic derivatives show promising chiroptical properties, both in term of circular dichroism (gabs 8 × 10 -3) and circularly polarized luminescence (glum 5 × 10 -3), thus demonstrating a practical application of our synthetic method.

Tuning the Reactivity of Peroxo Anhydrides for Aromatic C-H Bond Oxidation

Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C-H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

Synthesis of bromo-substituted 4-hydroxy[2.2]paracyclophanes and [2.2]paracyclophane-4,7-quinones as versatile chiral building blocks

Approaches to a number of bromo-substituted derivatives of 4-hydroxy[2.2]paracyclophane, including the regioselective mono- and dibromination of this phenol, were investigated. The applicability of the regioisomeric monobromo-substituted phenols for the synthesis of substituted [2.2]paracyclophane-4,7-quinones through a one-pot diazonium coupling/reduction/oxidation sequence was demonstrated. The compounds obtained possess various substitution patterns and could be used for the synthesis of a wide range of [2.2]paracyclophane derivatives by transformation of the bromine, hydroxy, and quinoid fragments.