18800-99-2

Basic information

• Product Name: 9,10-Anthracenedione, 2,6-bis(1,1-dimethylethyl)-
• Synonyms: 2,6-Di-tert-butyl-anthraquinone;2.6-Di-tert.-butyl-anthrachinon;2,6-Di-tert-butylanthraquinone;2,6-di-t-butylanthraquinone
• CAS NO: 18800-99-2
• Molecular Formula: C22H24O2
• Molecular Weight: 320.431
• Mol File: 18800-99-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 9,10-Anthracenedione, 2,6-bis(1,1-dimethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Anthracenedione, 2,6-bis(1,1-dimethylethyl)-(18800-99-2)
• EPA Substance Registry System: 9,10-Anthracenedione, 2,6-bis(1,1-dimethylethyl)-(18800-99-2)

Safety Data

• Hazardous Substances Data: 18800-99-2(Hazardous Substances Data)

Usage

General Description

9,10-Anthracenedione, 2,6-bis(1,1-dimethylethyl)-, also known as Menadione, is a synthetic organic compound with the molecular formula C17H12O3. It is a yellow crystalline solid that is commonly used as a precursor for the production of vitamin K in the pharmaceutical industry. Menadione exhibits antioxidant properties and has been used as a dietary supplement for birds and reptiles. However, it can be toxic if ingested in large quantities and has been banned for use in human dietary supplements due to potential health risks. In addition to its pharmaceutical applications, menadione is also used in the production of rubber and plastics.

Upstream product

• 62375-58-0 2,6-di-tert-butylanthracene 
• 106679-32-7 2(4-tert-Butylbenzoyl)-4-tert-butylbenzoic acid 
• 149917-01-1 (E)-2,2',6,6'-tetra-tert-butyl-9,9'-bianthronylidene 
• 18798-84-0 2,6,9-Tri-tert.-butyl-9-hydroxy-10-oxo-9,10-dihydro-anthracen 
• 120-12-7 anthracene 
• 88070-08-0 2-methyl-4',5-di-tert-butyldiphenylmethane 
• 18801-00-8 2-(t-butyl)anthracene 
• 4923-66-4 1,2,3,4-tetrahydro-9,10-anthraquinone 
• 84-47-9 2-tert-butylanthraquinine 
• 16430-37-8 10-hydroxy-3,10-di-t-butylanthrone 
• 18798-81-7 2-tert-Butyl-1,2-dihydro-anthraquinone 
• 92-84-2 10H-phenothiazine 
• 62337-63-7 (9-bromo-2,6-di-tert-butylanthracene) 

Relevant articles and documents

Hybrids of a 9-anthracenyl moiety and fluorescein as chemodosimeters for the detection of singlet oxygen in live cells

Singlet oxygen (1O2) plays an important role in human innate immune response, plant physiology and anticancer photodynamic therapy (PDT). Therefore, its monitoring by convenient and sensitive methods (e.g. by detecting a fluorescence signal) by using non-toxic reagents would be advantageous. Known fluorogenic 1O2-chemodosimeters can potentially consume reducing agents in cells leading to the generation of toxic side products that limit their applications. In this paper we report on a series of 9-anthracenyl-fluorescein hybrids, which do not require any reducing agents for their reaction with 1O2. The selected compound 8d at a very low concentration of 100 nM is able to detect 1O2 in live human promyelocytic leukemia HL-60 cells with over 35-fold fluorescence signal enhancement within only 20 min assay time. This chemodosimeter is not toxic to HL-60 cells at concentrations ≤1 μM (higher concentrations were not tested) even at long incubation times ≤48 h.

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Synthesis and electronic properties of sterically demanding N-arylphenothiazines and unexpected Buchwald-Hartwig aminations

(Chemical Equation Presented) Phenothiazine is coupled under Buchwald-Hartwig conditions with bromo anthracenes and perylene as substrates to give phenothiazine-anthracene and phenothiazine-perylene dyads and triads. Investigation of the electronic properties of these sterically demanding N-aryl phenothiazines by absorption and emission spectroscopy, cyclic voltammetry, and DFT calculations revealed that the individual chromophores are decoupled in the electronic ground state but show unique electronic communication in the excited state. For the anthracenyl-bridged diphenothiazine an intense electronic coupling of the phenothiazinyl units is detected upon oxidation. Besides, attempts to synthesize phenothiazine compounds with even more sterically demanding aryl substituents in the 10-position under N-arylation conditions gave rise to the formation of quite unexpected products of arylation and/or oxidative coupling. The folding angle of the phenothiazine in a consanguineous series correlates well with the first oxidation potential.

Synthesis of Alkyl-Substituted Helianthrones and Mesonaphthobianthrone by Highly Regioselective Photocyclization of Bianthronylidenes

The synthesis of the novel alkyl-substituted helianthrones 8a, c and mesonaphthobianthrone 9 by photocyclization of the corresponding bianthronylidenes 7a, b is described.Regioselectivity and scope of the photocyclizations of 7a and 7b depend on the substitution pattern.The structures of 7a and 8a have been established by X-ray crystallography and indicate an isomerization about the central double bond of 7a in the photoreaction.The structures of the protonated species of 8a and 9 are elucidated, and their optical absorption and emission behavior is examined.Key Words: Bianthronyls / Bianthronylidenes / Helianthrone / Mesonaphthobianthrone / Photocyclization