1625-81-6

Basic information

• Product Name: 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid
• Synonyms: 9,10-ethenoanthracene-11,12-dicarboxylic acid, 9,10-dihydro-; Tetracyclo[6.6.2.0~2,7~.0~9,14~]hexadeca-2,4,6,9,11,13,15-heptaene-15,16-dicarboxylic acid
• CAS NO: 1625-81-6
• Molecular Formula: C₁₈H₁₂O₄
• Molecular Weight: 292.2855
• Mol File: 1625-81-6.mol

Chemical Properties

• Boiling Point: 521.3°C at 760 mmHg
• Flash Point: 283.1°C
• Density: 1.488g/cm³
• Vapor Pressure: 1.08E-11mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid(1625-81-6)
• EPA Substance Registry System: 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid(1625-81-6)

Safety Data

• Hazardous Substances Data: 1625-81-6(Hazardous Substances Data)

Upstream product

• 56-23-5 tetrachloromethane 
• 644-80-4 cis-2-bromobutenedioic acid 
• 120-12-7 anthracene 
• 1625-82-7 dimethyl 2,3,5,6-dibenzobicyclo-<2.2.2>octa-2,5,7-triene-7,8-dicarboxylate 
• 1625-82-7 Dimethyl 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate 

Downstream Products

• 313996-01-9 N-(4-nitrophenyl)-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboximide 
• 120-12-7 anthracene 
• 2734-13-6 <2,3:5,6>dibenzo<2.2.2>octa-2,5,7-triene 

Relevant articles and documents

Iptycene-Derived pyridazines and phthalazines

(Chemical Equation Presented) The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of la

Probing substituent effects in aryl-aryl interactions using stereoselective diels-alder cycloadditions

Stereoselective Diels-Alder cycloadditions that probe substituent effects In aryl-aryl sandwich complexes were studied experimentally and theoretically. Computations on model systems demonstrate that the stereoselectivity In these reactions Is mediated by differential π-stacking Interactions In competing transition states. This allows relative stacking free energies of substituted and unsubstituted sandwich complexes to be derived from measured product distributions. In contrast to gas-phase computations, dispersion effects do not appear to play a significant role In the substituent effects, In accord with previous experiments. The experimental π-stacking free energies are shown to correlate well with Hammett σm constants (r= 0.96). These substituent constants primarily provide a measure of the Inductive electrondonating and -withdrawing character of the substituents, not donation into or out of the benzene π-system. The present experimental results are most readily explained using a recently proposed model of substituent effects In the benzene sandwich dimer In which the π-system of the substituted benzene Is relatively unimportant and substituent effects arise from direct through-space interactions. Specifically, these results are the first experiments to clearly show that OMe enhances these π-stacking interactions, despite being a π-electron donor. This Is In conflict with popular models In which substituent effects In aryl-aryl interactions are modulated by polarization of the aryl π-system.

Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: a joint experimental and theoretical study

A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.

Orbital unsymmetrization affects facial selectivities of Diels-Alder dienophiles

We investigated the Diels-Alder reactions of maleic anhydrides embedded in a dibenzobicyclo-[2.2.2]octatriene motif as a nonsterically biased dienophile. Substituents on a benzene ring in these dienophiles are far from the reaction center, providing a sterically equivalent π-face. Instead substituents can unsymmetrize the dienophilic π face through π* (anhydride)-π* (aromatic) orbital interactions. Electron-withdrawing substituents affect the facial bias and relative rates of these cycloadditions. The preference of the cycloadditions is opposite in direction to those observed in nucleophilic additions of 2-substituted-9,10-dihydro-9,10-ethanoanthracen-11-ones (dibenzobicyclo-[2.2.2]octadienones) and in electrophilic additions of 2-substituted 9,10-dihydro-9,10-ethenoanthracenes (dibenzobicyclo[2.2.2]octatrienes), though all of them have related dibenzobicyclic systems.

Aza-triptycene-based homoleptic tris-cyclometalated iridium(III) complexes as highly efficient phosphors in green OLEDs

Three homoleptic tris-cyclometalated iridium (III) complexes (Ir1–Ir3) based on a rigid aza-triptycene unit have been synthesized via a novel one-pot method. The coordination arrangement of Ir2 was revealed by single X-ray structural analysis and the mole

Ptycene pyridazine octadentate diplatinum complex phosphorescent material as well as preparation method and application thereof

The invention discloses a ptycene pyridazine octadentate diplatinum complex phosphorescent material as well as a preparation method and application thereof. The invention relates to a ptycene-modifiedpyridazine octadentate diplatinum complex bridged by oxygen atoms. According to a phosphorescent platinum complex disclosed by the invention, binuclear platinum is introduced into a rigid non-conjugated ptycene ligand, so that the light-emitting center is increased while the light-emitting efficiency reduction caused by a pi-pi accumulation effect is inhibited, and the light-emitting color of theplatinum complex phosphorescent material is adjusted to a great extent. Compared with mononuclear platinum complexes with the same light-emitting color, the obtained ptycene-modified pyridazine diplatinum complex has higher light-emitting efficiency, light-emitting brightness and thermal stability. According to an electroluminescent device provided by the invention, the light-emitting layer is prepared by adopting a spin-coating film preparation method under specific conditions, so that the cost is low, the operation is simple, the chemical property is stable, the light-emitting brightness and efficiency are high, and the realization of an efficient electroluminescent device is facilitated.

Iptycene pyridazine tetradentate platinum complex phosphorescent material, preparation method and application thereof

The invention discloses an iptycene pyridazine tetradentate platinum complex phosphorescent material, a preparation method and application thereof. The oxygen atom bridged pyridazine tetradentate platinum complex based on iptycene modification has a struc

Synthesis of novel aza-heterocyclic derivatives from diester and diacid chlorides having the dibenzobarrelene skeleton

When attempting to synthesize the symmetric aza-heterocyclic-substituted dibenzobarrelene derivatives from the 2-aminobenzimidazole (or 2-aminoimidazoline) with diacid chlorides and diester in the presence of various organic bases, different products were isolated in high yield. NMR spectroscopic analysis proved these products to be dibenzobarrelene-substituted fused benzimidazodiazepine, imidazolinediazepine, and dicarboxamides derivatives. Cyclic or noncyclic dicarboxamides with the dibenzobarrelene skeleton have been synthesized for the first time using these methods.

Ptycene-modified pyridazine iridium complex phosphorescent materials, and its preparation and application

The invention discloses ptycene-modified pyridazine iridium complex phosphorescent materials, and its preparation and application. According to the invention, ptycene-modified tricyclic metal iridium complexes and dicyclic metal iridium complexes with pyridazine cyclometalated ligand can be prepared by changing preparation conditions and have general structural formulas as shown in a formula (I) and a formula (II), respectively. Since rigid unconjugated ptycene structures wrapping iridium nucleuses are introduced into ligand in preparation of the phosphorescent iridium complexes, the luminous efficiency and color purity of the iridium complex phosphorescent materials are maximally improved. The prepared ptycene-modified tricyclic metal iridium complexes and dicyclic metal iridium complexes with the pyridazine cyclometalated ligand have high internal and external quantum yield, brightness and stability. A luminescent layer in an electroluminescent device provided by the invention is prepared by using a spin-coating film preparation method under specific conditions, and the prepared luminescent layer is simple to prepare, has low cost, stable chemical properties and high brightness and efficiency and is beneficial for preparation of a high-efficiency electroluminescent device.

Synthesis and effects on chloroquine susceptibility in Plasmodium falciparum of a series of new dihydroanthracene derivatives

To suggest a mechanism of action for drugs capable to reverse the chloroquine resistance, a new set of 9,10-dihydro-9,10-ethano and ethenoanthracene derivatives was synthesized and compounds were tested with the aim to assess their effect on chloroquine s