32745-55-4

Basic information

• Product Name: 1,4-Methano-1,4-dihydroanthracene-9,10-dione
• Synonyms: 1,4-Dihydro-1,4-methanoanthracene-9,10-dione;1,4-Methano-1,4-dihydroanthracene-9,10-dione;Tetracyclo[10.2.1.02,11.04,9]pentadecane-2(11),4(9),5,7,13-pentene-3,10-dione
• CAS NO: 32745-55-4
• Molecular Formula: C15H10O2
• Molecular Weight: 222.24
• Mol File: 32745-55-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 156 °C
• Boiling Point: 409°C at 760 mmHg
• Flash Point: 153.1°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 6.69E-07mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: 1,4-Methano-1,4-dihydroanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Methano-1,4-dihydroanthracene-9,10-dione(32745-55-4)
• EPA Substance Registry System: 1,4-Methano-1,4-dihydroanthracene-9,10-dione(32745-55-4)

Safety Data

• Hazardous Substances Data: 32745-55-4(Hazardous Substances Data)

Usage

Type

Chemical compound

Derivative of

Anthracene

Physical state

Yellow crystalline solid

Melting point

Around 346 degrees Celsius

Stability

Stable under normal conditions

Reactivity

Can react violently with strong oxidizing agents

Applications

a. Organic synthesis
b. Building block in organic electronic materials
c. Dye
d. Intermediate in pharmaceuticals and agrochemicals production
e. Potential use in organic electronic devices (e.g., organic field-effect transistors and organic light-emitting diodes)

InChI:InChI=1/C15H10O2/c16-14-10-3-1-2-4-11(10)15(17)13-9-6-5-8(7-9)12(13)14/h1-6,8-9H,7H2

Upstream product

• 24402-95-7 1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione 
• 24402-95-7 1,4,4a,9a-Tetrahydro-1,4-endomethylen-anthrachinon 
• 33741-23-0 endo-1,4,4a,9a-tetrahydro-1,4-methano-9,10-anthraquinone 
• 106-94-5 propyl bromide 
• 130-15-4 [1,4]naphthoquinone 
• 542-92-7 cyclopenta-1,3-diene 
• 134281-84-8 (+)-(SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone 
• 127709-12-0 exo tetracyclo<10.2.1.0^2,11.0^4,9>pentadeca-4,5,7,13-tetraene-3,10-dione 
• 52457-24-6 1,4-dihydro-1,4-methanoanthracene-9,10-diol 

Downstream Products

• 75171-64-1 C₁₅H₁₂O₃ 
• 75171-66-3 C₁₅H₁₂O₃ 

Relevant articles and documents

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.

Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes

Acid promoted ring opening of 1α,4α,4aα,9aα-tetrahydro-2β-3β- epoxy-l,4-methanoanthracene-9,10-dione and the corresponding 2-methyl derivative (i.e., 3a and 3b, respectively) afforded 4a and 4b in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 4b along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of 1α,4α-dihydro-4aα,9aα-epoxy- 1,4-methanoanthracene-9,10-dione (12) resulted in extensive skeltal rearrangement of the substrate, thereby affording 14 in low yield.

Asymmetric Diels-Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-naphthoquinones

The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored.The high ? facial diastereoselectivity observed can be reversed in the presence of ZnBr2.Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group.The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.