1627-06-1

Basic information

• Product Name: dianthrene
• Synonyms: dianthracene;dianthrene;5,6,11,12-Tetrahydro-5,12:6,11-di[1,2]benzenodibenzo[a,e]cyclooctene;9,10-(9,10-Dihydro-9,10-anthracenediyl)-9,10-dihydroanthracene;Paraanthracene;Paraanthrene
• CAS NO: 1627-06-1
• Molecular Formula: C₂₈H₂₀
• Molecular Weight: 356.4584
• Mol File: 1627-06-1.mol

Chemical Properties

• Melting Point: 244 °C
• Boiling Point: 409.8°Cat760mmHg
• Flash Point: 200°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 1.5E-06mmHg at 25°C
• Refractive Index: 1.693
• CAS DataBase Reference: dianthrene(CAS DataBase Reference)
• NIST Chemistry Reference: dianthrene(1627-06-1)
• EPA Substance Registry System: dianthrene(1627-06-1)

Safety Data

• Hazardous Substances Data: 1627-06-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H20/c1-2-10-18-17(9-1)25-19-11-3-4-12-20(19)26(18)28-23-15-7-5-13-21(23)27(25)22-14-6-8-16-24(22)28/h1-16,25-28H

Upstream product

• 120-12-7 anthracene 
• 121-69-7 N,N-dimethyl-aniline 
• 1564-64-3 9-Bromoanthracene 
• 92590-13-1 2,3:5,6-dibenzo-7,7,8,8-tetraisopropyl-7,8-disilabicycl<2.2.2>octa-2,5-diene 

Downstream Products

• 1625-84-9 9,10-dihydro-9,10-ethano-anthracene-11,11,12,12-tetracarbonitrile 
• 120-12-7 anthracene 
• 84-65-1 9,10-phenanthrenequinone 

Relevant articles and documents

Photoinduced electron transfer reactions of anthracene in CF3SO3H- CF3CO2H

Photolysis of anthracene in a mixture consisting of 2% CF3SO3H in CF3CO2H (w/w), where anthracene is partially protonated, gives a mixture of oxidized, neutral and reduced monomeric and dimeric products, initiation of this chemistry being photoinduced electron transfer from anthracene to protonated anthracene.

Photoreactivity of an exemplary anthracene mixture revealed by nmr studies, including a kinetic approach

Anthracenes are an important class of acenes. They are being utilized more and more often in chemistry and materials sciences, due to their unique rigid molecular structure and photoreactivity. In particular, photodimerization can be harnessed for the fabrication of novel photoresponsive materials. Photodimerization between the same anthracenes have been investigated and utilized in various fields, while reactions between varying anthracenes have barely been investigated. Here, Nuclear Magnetic Resonance (NMR) spectroscopy is employed for the investigation of the photodimerization of two exemplary anthracenes: anthracene (A) and 9-bromoanthracene (B), in the solutions with only A or B, and in the mixture of A and B. Estimated k values, derived from the presented kinetic model, showed that the dimerization of A was 10 times faster in comparison with B when compounds were investigated in separate samples, and 2 times faster when compounds were prepared in the mixture. Notably, the photoreaction in the mixture, apart from AA and BB, additionally yielded a large amount of the AB mixdimer. Another important advantage of investigating a mixture with different anthracenes is the ability to estimate the relative reactivity for all the reactions under the same experimental conditions. This results in a better understanding of the photodimerization processes. Thus, the rational photofabrication of mix-anthracene-based materials can be facilitated, which is of crucial importance in the field of polymer and material sciences.

Studies on photodimerization of 9-anthracenecarboxylic acid in its crystalline double salt with diamine

With the intention of obtaining uncommon head-to-head anthracene dimers, double salts of 9-anthracenecarboxylic acid (9-AC) with several diamines were photolyzed in the solid state. 9-AC underwent decarboxylation and reduction as well as dimerization. Although the head-to-tail dimer and an unsymmetrical dimer were obtained, the head-to-head one was not produced.

Photolysis of 2,3:5,6-Dibenzo-7,7,8,8-tetraisopropyl-7,8-disilabicycloocta-2,5-diene: Evidence for Cyclodimerization of a Disilene

Evidence for disilene dimerization was obtained by generating tetraisopropyldisilene from the title compound via the photochemical retrodiene process which produced the expected dimerization product, octaisopropylcyclotetrasilane (30percent), in addition to the H-abstraction product, 1,1,2,2-tetraisopropyldisilane (5percent).

Palladium(II)-Catalysed Aromatic Coupling and Substitution: Reactions of Anthracene, Phenanthrene, Diphenyl Ether and Diphenylamine

Anthracene when refluxed with Pd(OAc)2 in glacial HOAc affords 9,9'-bianthranyl (1) in poor yield along with traces of para-anthracene (2), the major product being anthraquinone.Addition of small amount of HClO4 in the above reaction totally suppresses the coupling reaction and gives anthraquinone as the exclusive product in much better yield.Treatment of anthracene with Pd(OAc)2 in the presence of Pb(OAc)4 affords 9-acetoxyanthracene (4), anthraquinone and dianthrone (5).The observed divergence in the product profile with anthracene in the above reactions from those with its lower homologues has been rationalised.Intramolekular Pd(II)-catalysed aryl-aryl coupling reactions of diphenyl ether and diphenylamine have also been studied.It is observed that while the former is almost unreactive towards Pd(OAc)2 in HOAc, the latter is converted into carbazole in fairly good yield under identical reaction condition.

Photochemical Reactions of Aromatic Compounds. XXXVI. The Photoreactions of Anthracene with Some Selected Tertiary Aromatic Amines in Polar Media

The photoreaction of anthracene witn N,N-dimethylaniline in acetonitrile gave 9-(p-dimethylaminophenyl)-9,10-dihydroanthracene in a good yield, along with 9,10-dihydroanthracene and 9,9',10,10'-tetrahydro-9,9'-bianthryl.This photoreaction was found to depend on the polarity of the solvent as well as on its protic or aprotic nature.With N,N-dimethyl-m-toluidine, a similar 1 : 1 adduct was obtained, while the reduced anthracenes were mainly formed in the photoreactions with N,N-dimethyl-o- and p-toluidines.The mechanisms were discussed in terms of the dissociation into the ion radical as well as their reactivities.