434-85-5

Basic information

• Product Name: Bianthrone
• Synonyms: BIANTHRONE;dianthraquinone;DIANTHRONE;10-(10-oxo-9(10h)-anthracenylidene)-9(10h)-anthracenon;Bianthvone;10,10'-bianthrone;BIANTHRONE CRYSTALLINE;BIANTHRONE(RG)
• CAS NO: 434-85-5
• Molecular Formula: C₂₈H₁₆O₂
• Molecular Weight: 384.43
• EINECS: 207-106-8
• Product Categories: Industrial/Fine Chemicals;Colours, Dyes, Indicators & Pigments
• Mol File: 434-85-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 451.11°C (rough estimate)
• Flash Point: 208.41 °C
• Appearance: yellow powder
• Density: 1.2122 (rough estimate)
• Vapor Pressure: 4.85E-13mmHg at 25°C
• Refractive Index: 1.4480 (estimate)
• Storage Temp.: 2-8°C
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• CAS DataBase Reference: Bianthrone(CAS DataBase Reference)
• NIST Chemistry Reference: Bianthrone(434-85-5)
• EPA Substance Registry System: Bianthrone(434-85-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 434-85-5(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

InChI:InChI=1/C28H16O2/c29-27-21-13-5-1-9-17(21)25(18-10-2-6-14-22(18)27)26-19-11-3-7-15-23(19)28(30)24-16-8-4-12-20(24)26/h1-16H

Upstream product

• 56-23-5 tetrachloromethane 
• 1560-32-3 10-bromo-10H-anthracen-9-one 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 90-44-8 anthracen-9(10H)-one 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 434-84-4 bianthronyl 
• 7664-93-9 sulfuric acid 
• 529-86-2 9-anthrol 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 84-65-1 9,10-anthraquinone radical anion 
• 1347684-33-6 (E)-1-(anthracen-9-yl)-3-(pyridin-4-yl)prop-2-en-1-one 

Downstream Products

• 613-31-0 9,10-dihydroanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 53418-60-3 10,10'-diphenyl-10H,10'H-[9,9']bytrancenylidene-10,10'-diol 
• 1191886-63-1 10,10'-dihydroxy-10,10'-bis(2,4,6-trimethylphenyl)-9,9'-bianthracenylidene 
• 1192537-31-7 C₆₂H₇₆O₄Si₂ 
• 475-64-9 phenanthro[1,10,9,8-opra]prylene-7,14-dione 
• 190-39-6 bisanthene 
• 7722-84-1 dihydrogen peroxide 
• 120207-61-6 10,10'-bis-(4-chloro-phenyl)-10H,10'H-[9,9']bianthrylidene-10,10'-diol 

Relevant articles and documents

9-Anthracenyl-substitued pyridyl enones revisited: Photoisomerism in ligands and silver(i) complexes

In solution, (E) to (Z)-isomerism is facile both in 3-(9-anthracenyl)-1- (pyridin-4-yl)propenone, 2, and in its silver(i) complex [Ag(2) 2]+. The crystal structures of (E)-2, (Z)-2 and [Ag{(E)-2}2][SbF6] are presented, and the roles of edge-to-face and face-to-face π-interactions in the lattice are discussed. Solution NMR spectroscopic data suggest that the driving force for (E) to (Z) isomerization is intramolecular π-stacking of the pyridine and anthracene domains. The reversed enone 3-(9-anthracenyl)-1-(pyridin-4-yl)propen-3-one, (E)-3, and the silver(i) complex [Ag{(E)-3}2][SbF6] have been prepared and characterized, including a single crystal X-ray determination of the latter. Surprisingly, no π-stacking between anthracene or pyridine domains is observed in the solid state, and the crystal packing is dominated by Ag...F, CHanthracene...π-pyridine and CH...F interactions. In contrast to (E)-2 and [Ag{(E)-2}2]+, neither (E)-3 nor [Ag{(E)-3}2]+ undergoes photoisomerization in solution.

ELECTRON-TRANSFER REACTIONS AND ASSOCIATED CONFORMATIONAL CHANGES. STUDIES OF BIANTHRONE REDUCTION VIA HOMOGENEOUS REDOX CATALYSIS.

The catalyzed reductions of bianthrone (1) and 1,1 prime -dimethylbianthrone have been quantitatively characterized in dimethylformamide solvent. The technique that was employed involves the generation of anion radicals of various quinones at a mercury electrode. As they diffuse near the electrode, these anion radicals can transfer an electron to A form of the bianthrone. At low catalyst concentrations, the rate of reduction of 1 is governed by the forward electron-transfer reaction for each of five quinones. the back reaction was shown to be diffusion controlled. The results were compared with radiolysis studies in a different medium. The present work was the result of interest in the significant role of molecular conformation in the thermodynamics and kinetics of electron-transfer reactions. Refs.

Electron-Transfer Reactions and Conformational Changes Associated with the Reduction of Bianthrone

The electrochemical reduction of the low-temperature A form of bianthrone (1A) at a platinum cathod in DMF proceeds in a two-electron, irreversible reaction, giving the dianion 3B which is structurally similar to the high-temperature B form of bianthrone (1B), having two planar ring system twisted about the central connecting bond.The overall reduction involves a large structural change.By contrast, 3B is rapidly and reversibly oxidized to a structurally similar anion radical, 2B, and then to 1B which is not stable at room temperature and converts to 1A as it diffuses away from the electrode.This scheme was confirmed by cyclic voltammetry and transmission-mode spectroelectrochemistry.Rate constants for both the 1A->1B and 1B->1A reactions were determined, and upper limits were put on the rate constants for the direct electrochemical reduction of 1A to 2B or 3B.

Facile synthesis and lateral πnsion of bisanthenes

The improved Scholl reaction allows for the direct cyclization of anthracene oligomers to give bisanthene, teranthene, and quateranthene. Furthermore, a variety of πnded bisanthenes are obtained by the Diels-Alder cyclo-addition of bisanthene with several arynes. These reactions would allow us to synthesize various size- and shape-controlled polyperiacenes.

An easy synthesis of thermochromic ethylenes under microwave irradiation

Thermochromic ethylenes were obtained by the reaction of anthrone with tricyclic ketones or terephthaldehyde in DMF in the presence of potassium ter-butoxide under reflux (8h) or under microwave irradiation (10 min.).