82-86-0

Basic information

• Product Name: Acenaphthenequinone
• Synonyms: 1,2-Acenaphthalenedione;1,2-Acenaphthenedione;1,2-Acenaphthenequinone;Acenaphthenedione;acenaphthylene-1,2-quinone;acenaphthylenequinone;AKOS 92207;ACENAPHTHAQUINONE
• CAS NO: 82-86-0
• Molecular Formula: C₁₂H₆O₂
• Molecular Weight: 182.17
• EINECS: 201-441-3
• Product Categories: Pharmaceutical Intermediates;Anthraquinones, Hydroquinones and Quinones;C11 to C12;C11 to C12G Proteins and Cyclic Nucleotides;Cyclic Nucleotide Metabolism;Guanylyl Cyclase Inhibitors;Carbonyl Compounds;Ketones
• Mol File: 82-86-0.mol

Chemical Properties

• Melting Point: 249-252 °C (dec.)(lit.)
• Boiling Point: 67 C
• Flash Point: 150.2 °C
• Appearance: Ochre/Powder and Granules
• Density: 1.4800
• Refractive Index: 1.6086 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• Water Solubility: INSOLUBLE
• BRN: 879172
• CAS DataBase Reference: Acenaphthenequinone(CAS DataBase Reference)
• NIST Chemistry Reference: Acenaphthenequinone(82-86-0)
• EPA Substance Registry System: Acenaphthenequinone(82-86-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 2920
• WGK Germany: 3
• RTECS: AB1024500
• TSCA: Yes
• Hazardous Substances Data: 82-86-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Acenaphthenequinone is used as an intermediate in the manufacturing of dyes and pharmaceuticals. It plays a crucial role in the synthesis of various drugs and dyes, contributing to the development of new and improved products in the pharmaceutical industry.
Used in Chemical Research:
Acenaphthenequinone is used as a drug and therapeutic agent in chemical research. Its unique chemical properties make it a valuable compound for studying various biological and chemical processes, leading to the discovery of new therapeutic agents and applications.
Used in Bioimaging:
Acenaphthenequinone is used in the preparation of turn-on sensors for cysteine/homocysteine and its application in bioimaging. This allows for the detection and monitoring of these important biomolecules, providing valuable insights into their role in various biological processes and diseases.
Used in Acetylcholinesterase Inhibition:
Acenaphthenequinone is used in the preparation of acetylcholinesterase inhibitory agents. These agents are important in the treatment of various neurological disorders, such as Alzheimer's disease, by inhibiting the enzyme acetylcholinesterase and increasing the levels of the neurotransmitter acetylcholine in the brain.

Safety Profile

Moderately toxic by an unspecifiedroute. When heated to decomposition it emits acrid smokeand irritating vapors.

Purification Methods

Extract it with, then recrystallise it twice from *C6H6. Dry it in vacuo. [LeFevre et al. J Chem Soc 974 1963, Beilstein 7 IV 2498.]

InChI:InChI=1/C12H8O2/c13-10-6-8-3-1-2-7-4-5-9(11(7)8)12(10)14/h1-3,6H,4-5H2

Upstream product

• 33489-49-5 acenaphthenequinone monoxime 
• 5116-63-2 phenalene-1,2,3-trione 
• 18931-20-9 2,2-dihydroxy-phenalene-1,3-dione 
• 24040-40-2 2-(4-dimethylamino-phenylimino)-acenaphthen-1-one 
• 83-32-9 acenaphthene 
• 16269-27-5 2-bromoacenaphthylen-1(2H)-one 
• 712-74-3 1,2,4,5-tetracyanobenzene 
• 2008-77-7 2-diazoacenaphthen-1-one 
• 103457-73-4 Ethyl 2-oxo-3'-phenylspiro-4'-carboxylate 
• 13093-45-3 acenaphthyne 
• 62-75-9 N-Nitrosodimethylamine 
• 208-96-8 acenaphthylene 
• 2235-15-6 1(2H)-acenaphthylenone 
• 14209-08-6 1,2-dibromoacenaphthene 

Downstream Products

• 6252-78-4 2-(2-oxo-acenaphthen-1-ylidene)-benzo[b]thiophen-3-one 
• 856357-20-5 2,2-bis-(4-hydroxy-3-methyl-phenyl)-acenaphthen-1-one 
• 600727-64-8 2,2-bis(4-dimethylaminophenyl)acenaphthen-1-one 
• 56330-01-9 acenaphthene-1,2-dione-mono-(methyl-phenyl-hydrazone) 
• 13362-59-9 9-methyl-acenaphtho[1,2-b]quinoxaline 
• 72851-41-3 7,12-dicyano-benzofluoranthene 
• 111295-29-5 2-hydroxy-2-phenylethynyl-acenaphthen-1-one 
• 1932-06-5 acenaphthene-1,2-dione-bis-phenylhydrazone 
• 13152-81-3 acenaphthenquinone monophenylhydrazone 
• 73042-90-7 4-(7H-acenaphtho[1,2-d]imidazol-8-yl)-N,N-dimethyl-aniline 
• 134859-12-4 9-nitro-acenaphtho[1,2-b]quinoxaline 

Relevant articles and documents

The special role of B(C6F5)3 in the single electron reduction of quinones by radicals

In the presence of two molar equiv. of B(C6F5)3p-benzoquinone reacts with persistent radicals TEMPO, trityl or decamethylferrocene by single electron transfer to give doubly O-borylated benzosemiquinone radical anions with

Degradation of acenaphthylene and anthracene by chemically modified laccase from Trametes versicolor

We are studying the chemically modified laccase from Trametes versicolor for use in the in vitro oxidation of two polycyclic aromatic hydrocarbons (PAHs), acenaphthylene and anthracene, in combination with 2,2′-azino-bis- (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) as a redox mediator. The results indicate that the maleic anhydride modified laccase (MA-Lac) improved the stability of laccase to temperature, pH and storage time compared with the free enzyme. After incubation for 72 h, the MA-Lac-ABTS system oxidized acenaphthylene and anthracene to more than 70% from the reaction mixture. This journal is the Partner Organisations 2014.

Kinetic studies of acenaphthene oxidation catalyzed by N-Hydroxyphthalimide

The acenaphthene oxidation with molecular oxygen in the presence of N-hydroxyphthalimide (NHPI) has been investigated. It is shown that the main oxidation product is acenaphthene hydroperoxide. The phthalimide-N-oxyl (PINO) radical has been generated in situ from its hydroxyimide parent, NHPI, by oxidation with iodobenzenediacetate. The rate constant of H-abstraction (k H) from acenaphthene by PINO has been determined spectroscopically in acetonitrile. The kinetic isotope effect and the activation parameters have also been measured. On the basis of the results of our studies and available published literature data, a plausible mechanism for the oxidation process of acenaphthene with dioxygen catalyzed by NHPI was discussed.

Design, synthesis and characterization of a modular bridging ligand platform for bio-inspired hydrogen production

Synthesis and characterization of a novel type of ambident bridging ligands joining together the functional prerequisites for visible-light absorption, photoinduced electron transfer and catalytic proton reduction is presented. This class of compounds consists of a chromophoric 1,2-diimine-based π-acceptor site and a rigid polyaromatic dithiolate chelator. Due to the presence of a common conjugated linker moiety with an intrinsic two-electron redox reactivity and a suitable orbital coupling of the subunits, a favourable situation for vectorial multielectron transfer from attached electron donors to a catalytic acceptor site is provided. As an example for the application of this kind of bifunctional ligand systems, a [FeFe]-hydrogenase enzyme model compound is prepared and structurally characterized. Electrocatalytic hydrogen formation with this complex is demonstrated.

New recoverable organoselenium catalyst for hydroperoxide oxidation of organic substrates

New benzisoselenazol-3(2H)-one covalently bounded to a silica support was synthesized and characterized. It was used as an effective, selective, and easy-to-regenerate catalyst for t-BuOOH and H2O2 oxidation of alkyl arenes to alkyl aryl ketones, aromatic aldehydes to arene carboxylic acids, and sulfoxides and/or sulfones. Copyright Taylor & Francis Group, LLC.

Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can

A study was conducted to demonstrate the similarity of reactivity between o-iodoxybenzoic acid (IBX), an oxidative agent of vicinal diols and Des-Martin periodinane (DMP). The study examined IBX-mediated oxidative cleavage of tert,tert-1,2-diols and discovered pathways that favored fragmentation of sec,sec-1,2-diols, which produce non-cleavage products. It was observed that IBX can be employed to perform oxidative cleavage of 1,2-diols similar to DMP by simple variation of solvent and temperature. It was also observed that protonation of 10-1-4 species of diols may suppress the nucleophilic attack, leading to the production of ketol to achieve oxidative cleavage of sec,sec-1,2-diols that yield non-cleavage products with IBX in DMSO. TFA was used as a significant source of protons and a better solvent of IBX to conduct protonation of diols. A variety of sec,sec,tert,tert and sec,tert syn-1,2-diols underwent oxidative cleavage effectively, using TFA as a solvent.

Oxidations with IBX: Benzyl halides to carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones

A variety of benzyl halides were converted to the corresponding aldehydes/ketones in respectable yields by IBX in DMSO at 65°C. The bromohydrin reaction of olefins using NBS-H2O in DMSO can be nicely adapted to IBX-mediated oxidation of benzyl halides in such a way that olefins are converted to the corresponding 1,2-diketones in good isolated yields in one-pot.

Therapeutics for chemokine mediated diseases

The invention provides therapeutic and biological uses of chemokine-receptor-binding compounds (including chemokine receptor ligands such as chemokine receptor agonists or antagonists), such as tricyclic phenanthrene derivatives, including uses in the treatment of disease states mediated by chemokines. The relevant chemokines may for example be monocyte chemoattractant protein-one (MCP-1) or interleukin-8 (IL-8), and the relevant chemokine receptors may for example be corresponding chemokine receptors (CCR-2, CCR-4, CXCR-1, and CXCR-2). In other aspects, the invention provides corresponding pharamaceutical compositions and therapeutic methods. In one aspect, for example, the invention provides for the use of phenanthrene-9,10-dione in the treatment of multiple sclerosis.

Catalytic oxidation of acenaphthene and its derivatives in acetic acid

The chemistry of formation of products of acenaphthene oxidation in the presence of the catalyst containing both manganese and cobalt bromides under batch conditions is discussed. The main reaction products are acenaphthene quinone, acenaphthenol-9, trans-acenaphthylene glycol, naphthalide, and naphthalic anhydride. The sequence of reactions leading to the final products is established. It is shown that the main oxidation product in the presence of the manganese-based catalyst is naphthalic anhydride, and the main product in the presence of the cobalt-based catalyst is acenaphthene quinone. The process and engineering techniques providing for the high overall and fractional yields of the desired products are discussed.

Reactions of hydroxyl radicals and ozone with acenaphthene and acenaphthylene

Acenaphthene and acenaphthylene are polycyclic aromatic hydrocarbons (PAHs) emitted into the atmosphere from a variety of incomplete combustion sources such as diesel exhaust. Both PAHs are present in the gas phase under typical atmospheric conditions and