146885-81-6

Basic information

• Product Name: 3,8-Dimethylacenaphthenequinone
• Synonyms: 3,8-Dimethylacenaphthenequinone
• CAS NO: 146885-81-6
• Molecular Formula: C₁₄H₁₀O₂
• Molecular Weight: 210.228
• Mol File: 146885-81-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 206.0 to 210.0 °C
• Boiling Point: 408.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.310±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,8-Dimethylacenaphthenequinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8-Dimethylacenaphthenequinone(146885-81-6)
• EPA Substance Registry System: 3,8-Dimethylacenaphthenequinone(146885-81-6)

Safety Data

• Hazardous Substances Data: 146885-81-6(Hazardous Substances Data)

Usage

Description

3,8-Dimethylacenaphthenequinone is an organic compound characterized by its quinone structure with two methyl groups at the 3rd and 8th positions on the acenaphthene ring. It is a versatile intermediate in the synthesis of various complex organic molecules, particularly those with fluorinated or trifluoromethylated functionalities.

Uses

Used in Organic Synthesis:
3,8-Dimethylacenaphthenequinone is used as a key intermediate for the synthesis of fluorinated and trifluoromethylated corannulenes. These complex organic molecules have potential applications in various fields, such as materials science, pharmaceuticals, and chemical research.
Used in Materials Science:
In the field of materials science, 3,8-Dimethylacenaphthenequinone is used as a precursor for the development of novel materials with unique properties, such as enhanced stability, reactivity, or electronic characteristics. The fluorinated and trifluoromethylated corannulenes derived from this intermediate can be utilized in the creation of advanced materials for various applications, including electronics, energy storage, and sensors.
Used in Pharmaceutical Research:
3,8-Dimethylacenaphthenequinone plays a crucial role in the pharmaceutical industry as a building block for the development of new drugs with improved efficacy and selectivity. The fluorinated and trifluoromethylated corannulenes synthesized from this intermediate can be further modified and optimized to target specific biological pathways or receptors, leading to the discovery of innovative therapeutic agents for various diseases and conditions.

Upstream product

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• 56137-97-4 3,8-dimethyl-1-acenaphthenone 

Downstream Products

• 5821-51-2 Coarannulen 
• 1383793-92-7 C₂₈H₁₆F₅NO₂ 
• 146885-82-7 6,7-dihydro-6-hydroxy-7,9-dimethyl-8H-cyclopenta[a]acenaphthylene-8-one 
• 1041416-82-3 1,2,5,6-tetra(phenylethynyl)corannulene 

Relevant articles and documents

Synthesis of corannulene and alkyl derivatives of corannulene

Synthesis of corannulene and alkyl corannulene derivatives has been accomplished using solution-phase chemistry. The key step in the synthesis is the coupling of benzylic bromides of 1,6,7,10-tetraalkylfluoranthene derivatives by low-valent titanium to construct the corannulene nucleus. The use of low-valent titanium represents a viable alternative to flash vacuum pyrolysis methods previously developed. Corannulene (1), methylcorannulene (8), three different dimethylcorannulenes (2, 3, 5), two different tetramethylcorannulenes (4, 6), acecorannulylene (7), C5h symmetric pentamethylcorannulene (9), and decamethylcorannulene (10) have been prepared using low-valent titanium carbon-carbon coupling chemistry and halogen for alkyl exchange chemistry mediated by trimethylaluminum and catalytic nickel salts.

Synthesis and Properties of Monosubstituted Ethynylcorannulenes

The solution-phase synthesis of corannulene has been modified and it is now possible to prepare multi gram quantities of corannulene more efficiently, with considerably less toxic reagents. Cross-coupling of bromocorannulene with TMS-acetylene and phenylacetylene affords novel ethynyl-containing corannulene derivatives. Deprotection of TMS-ethynyl corannulene affords the naked alkyne, which can be cross-coupled with pentafluoroiodobenzene and bromocorannulene to afford the appropriate alkyne derivatives. The photophysical properties of this new and novel family of alkyne-containing corannulene derivatives has been evaluated and all of the new derivatives exhibit low to moderate quantum efficiencies.

Stack the Bowls: Tailoring the Electronic Structure of Corannulene-Integrated Crystalline Materials

We report the first examples of purely organic donor–acceptor materials with integrated π-bowls (πBs) that combine not only crystallinity and high surface areas but also exhibit tunable electronic properties, resulting in a four-orders-of-magnitude conductivity enhancement in comparison with the parent framework. In addition to the first report of alkyne–azide cycloaddition utilized for corannulene immobilization in the solid state, we also probed the charge transfer rate within the Marcus theory as a function of mutual πB orientation for the first time, as well as shed light on the density of states near the Fermi edge. These studies could foreshadow new avenues for πB utilization for the development of optoelectronic devices or a route for highly efficient porous electrodes.

Self-assembly of fivefold-symmetric molecules on a threefold-symmetric surface

Buckybowls: The adsorption of penta-tert-butylcorannulene, a molecule with fivefold symmetry, on Cu(111), a surface with threefold symmetry, is investigated by scanning tunneling microscopy complemented by structure calculations. The symmetry mismatch is