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
• Article Data: 23

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

Chemical Properties

ochre powder and granules

Uses

Acenaphthenequinone is used in the preparation of acetylcholinesterase inhibitory agents. It is also used in the preparation of turn-on sensors for cysteine/homocysteine and its application in bioimaging. Further, it is used as an intermediate in manufacturing of dyes and pharmaceuticals. In addition to this, it is used in chemical research as a drug and therapeutic agent.

Definition

ChEBI: A member of the class of orthoquinones that is the 1,2-dioxo derivative of acenaphthene.

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

• 5116-63-2 phenalene-1,2,3-trione 
• 24040-40-2 2-(4-dimethylamino-phenylimino)-acenaphthen-1-one 
• 83-32-9 acenaphthene 
• 16269-27-5 2-bromoacenaphthylen-1(2H)-one 
• 103457-73-4 Ethyl 2-oxo-3'-phenylspiro-4'-carboxylate 
• 33489-49-5 acenaphthenequinone monoxime 
• 7664-93-9 sulfuric acid 
• 1932-08-7 N,N’-dihydroxy-1,2-acenaphthylenediimine 
• 7446-70-0 aluminium trichloride 
• 13152-85-7 2,2-Dichlor-1(2H)-acenaphthenon 
• 7732-18-5 water 
• 4364-44-7 1,2-dibenzyliden-acenaphthene 
• 91-20-3 naphthalene 
• 20033-74-3 bis(phenylimidoyl)chloride 

Downstream Products

• 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 
• 1932-06-5 acenaphthene-1,2-dione-bis-phenylhydrazone 
• 13152-81-3 acenaphthenquinone monophenylhydrazone 
• 134859-12-4 9-nitro-acenaphtho[1,2-b]quinoxaline 
• 424-88-4 (+/-)-1r,2t-bis-(4-fluoro-phenyl)-acenaphthenediol-(1,2c) 
• 238-06-2 8,9-Benzoacenaphtho<1,2-b>chinoxalin 
• 34453-48-0 6b-hydroxy-9-phenyl-6b,7-dihydro-cyclopent[a]acenaphthylen-8-one 
• 115933-58-9 1,2-di-o-tolyl-acenaphthene-1,2-diol 
• 6566-38-7 cis-1,2-dihydroxy-1,2-dimethyl-1,2-dihydroacenaphthalene 
• 6566-38-7 trans-1,2-dihydroxy-1,2-dimethyl-1,2-dihydroacenaphthalene 

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

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.

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.