7396-21-6

Usage

Uses

Used in Organic Synthesis:
1-(Anthracen-1-yl)ethanone is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Dye and Pigment Production:
As a precursor, anthrone is utilized in the production of dyes and pigments, enhancing the color properties and stability of these products in different applications.
Used in Organic Chemistry Research:
Due to its fluorescence properties, 1-(anthracen-1-yl)ethanone is employed as a fluorescent dye in the study of organic chemistry, aiding in the investigation of molecular structures and interactions.
Used in Biological Applications:
Anthrone's fluorescent properties also make it suitable for use in biological applications, where it can be employed to label and track biological molecules, contributing to advancements in life sciences research.

InChI:InChI=1/C16H12O/c1-11(17)15-8-4-7-14-9-12-5-2-3-6-13(12)10-16(14)15/h2-10H,1H3

Upstream product

• 120-12-7 anthracene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 607-42-1 anthracene-1-carboxylic acid 
• 105-53-3 diethyl malonate 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 71-43-2 benzene 

Downstream Products

• 66291-35-8 1-ethylanthracene 
• 42081-41-4 1-(Hydroxymethyl)triptycen 
• 42081-42-5 1-(Chlormethyl)-triptycen 
• 1444102-97-9 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(cyclohexylcarbamothioyl)hydrazono)butanoate 
• 1444103-01-8 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(phenylcarbamothioyl)hydrazono)butanoate 
• 1444103-09-6 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(phenylcarbamothioyl)hydrazono)butanoate 
• 1444103-02-9 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(p-tolylcarbamothioyl)hydrazono)butanoate 
• 1444103-10-9 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(p-tolylcarbamothioyl)hydrazono)butanoate 

Relevant academic research and scientific papers

Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity

A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 μM. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.

Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents

A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structure-based 3-D QSAR models for 6f, 6e, 6i and 6l describe pro-apoptotic activity against caspase-3.

1 - [...] synthetic preparation method

The invention discloses a 1 - [...] synthetic preparation method, comprises the following steps: S1) will anthracene and acetyl chloride is dissolved in the solvent, and the catalysis of a Lewis acid, reaction to obtain the 1 - b [...]; S2) 1 - b [...] through oxidation reaction, to obtain 1 - carboxylic acid anthracene; S3) under the action of the acyl, firstly the 1 - anthracene acid radical chloride acid, to remove the surplus solvent, followed by reaction with cyanide, to produce the target compound 1 - cyanate anthracene. The present invention provides 1 - [...] synthetic preparation method, in order to low-cost transfer catalyst, acetyl chloride as the raw material, after three step synthesis of simple and convenient operation, and then after treatment and purification, can prepare and get the purity 98% or more of 1 - [...], not only the production cost is low, the experimental steps are few, simple operation, and after the simple purification, the purity can reach 98% above, can fully meet the T - 2 toxin of the derivatization detection, greatly reduce the T - 2 toxin detection cost.

Concerted Interplay of Excimer and Dipole Coupling Governs the Exciton Relaxation Dynamics in Crystalline Anthracenes

A combined theoretical and experimental investigation into the role of concerted long- (dipole coupling) and short-range (orbital overlap mediated excimer) electronic interactions in modulating the emission of six crystalline acetylanthracenes (1–3) is reported. Friedel–Crafts acylation of anthracene rendered crystalline acetylanthracenes with discrete close packing, varied orbital overlap, and resultant distinct emission (blue–green–yellow) from cooperative excimer and dipole coupling. Time-resolved emission spectroscopy (TRES) studies and the Kasha's exciton theory based quantitative estimation of dipole coupling (mean-field approximation) substantiates the exciton dynamics in crystalline 1–3. Extension of the Kasha's exciton model beyond the traditional nearest-neighbor approach, and consistent agreement among the computed spectral shifts and TRES temporal components, corroborate a holistic approach to decipher the exciton relaxation dynamics in the molecular assembly of novel photonic materials.

Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity

A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino

Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group

A series of novel anthraquinone-thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5

Reversible Friedel-Crafts acylations of anthracene: Rearrangements of acetylanthracenes

Treatment of 1-acetylanthracene (1-AcAN) and 9-acetylanthracene (9-AcAN) with PPA at 80-120 °C leads to the nearly complete conversion of these isomers into 2-acetylanthracene (2-AcAN), an illustration of the Agranat-Gore rearrangement of polycyclic aromatic ketones (PAKs). Ab initio MP2/6-31(d) calculations predict the following order of stabilities: for O-complexes: 9-AcAN>1-AcAN>2-AcAN; for ketones: 2-AcAN>1-AcAN>9-AcAN; for O-protonated ketones: 2-AcAN>1-AcAN>9-AcAN. Thus, 9-AcAN is the kinetically controlled product, whereas 2-AcAN is the thermodynamically controlled product. No reverse rearrangements of 2-AcAN to either 9-AcAN or 1-AcAN and of 1-AcAN to 9-AcAN were observed. The results strengthen the pattern of reversibility in Friedel-Crafts acylations of PAHs.

Unusual inhibition effect of 1-(1-naphthyl)-1-methylethylhydroperoxide on the liquid-phase oxidation of isopropylarenes. GC-MS and theoretical studies of the thermal decomposition of 1-naphthyl- and 1-anthryl-1- methylethylhydroperoxides

All five possible 1-aryl-1methylethylhydroperoxides derived from naphthalene and anthracene were synthesized and their thermal decomposition in GC-MS conditions was investigated to explain the unusual inhibition effect of 1-(1-naphthyl)-1-methylethylhydroperoxide on the liquid-phase oxidation of isopropylarenes. 2-(1-Aryloxy)propenes were identified as the main decomposition products of 1-(1-naphthyl)-1-methylethylhydroperoride and 1-(1-anthryl)-1- methylethylhydroperoxide. The relatively unstable 2-aryloxypropenes have thus far never been described as thermal decomposition products of 1-aryl-1-methylethylhydroperoxides. The plausible mechanism of the formation of 2-(1-aryloxy)propenes was proposed on the basis of AM-1 calculations of the possible rearrangement paths of the alkoxy radicals derived from the investigated hydroperoxides. The mechanism explains the inhibition effect of 1-(1-naphthyl)-1-methylethylhydroperoxide on the oxidation of isopropylarenes.

Kinetics and Mechanism of Friedel-Crafts Acetylation of Anthracene in 1,2-Dichloroethane

The kinetics and mechanism of Friedel-Crafts acetylation of anthracene in 1,2-dichloroethane, have been studied.The reaction is found to be of an overall second order, first order with respect to anthracene and first order with respect to the acetylating reagent.The specific rates of the reaction have been determined at five temperatures in the range 7 deg C to 14 deg C.The activation parameters have been calculated and reported.The mechanism proposed involves acetylation via the acetylating oxonium complex between acetylchloride and aluminium chloride.