5445-55-6

Basic information

• Product Name: TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL
• Synonyms: TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL;trans-9,10-dihydro-9,10-ethanoanthracene-11,12-di
• CAS NO: 5445-55-6
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.33
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 5445-55-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 203-205 °C(lit.)
• Boiling Point: 453.9°Cat760mmHg
• Flash Point: 217.1°C
• Appearance: /
• Density: 1.212g/cm³
• Vapor Pressure: 4.97E-09mmHg at 25°C
• Refractive Index: 1.629
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL(5445-55-6)
• EPA Substance Registry System: TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL(5445-55-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5445-55-6(Hazardous Substances Data)

Usage

Description

TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL is a complex organic compound with a unique molecular structure. It is characterized by its anthracene core, which is a tricyclic aromatic hydrocarbon, and the presence of a dihydro and ethano bridge. The molecule also features two hydroxyl groups at the 11 and 12 positions, which can participate in various chemical reactions and interactions.

Uses

Used in Chemical Synthesis:
TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL is used as a key intermediate in the synthesis of dibenzo[b,f]oxepin scaffolds. This application is particularly relevant in the field of organic chemistry, where the compound serves as a building block for the creation of more complex and functionalized molecules.
In the Synthesis of Dibenzo[b,f]oxepin Scaffolds:
TRANS-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIMETHANOL is used as a starting material for the Ullmann-type etheration reaction. This reaction involves the formation of an ether linkage between the hydroxyl groups of the compound and another aromatic or heteroaromatic molecule. The resulting dibenzo[b,f]oxepin scaffolds are valuable in various applications, such as pharmaceuticals, agrochemicals, and materials science, due to their diverse chemical properties and potential for further functionalization.

InChI:InChI=1/C18H18O2/c19-9-15-16(10-20)18-12-6-2-1-5-11(12)17(15)13-7-3-4-8-14(13)18/h1-8,15-20H,9-10H2/t15-,16-,17?,18?/m1/s1

Upstream product

• 36326-57-5 racemic-9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid 
• 41204-41-5 dimethyl 2,3:5,6-dibenzobicyclo<2.2.2>octa-2,5-diene-trans-7,8-dicarboxylate 
• 83742-19-2 trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester 
• 120-12-7 anthracene 
• 23194-04-9 trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid dimethyl ester 
• 33216-00-1 (11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid 
• 78392-59-3 di-<(1S)-endo>-(-)-borneyl fumarate 
• 593279-33-5 di(+)-isomenthyl fumarate 
• 593279-35-7 di(+)-fenchyl fumarate 
• 593279-34-6 di(-)-isopulegyl fumarate 
• 23194-05-0 9,10-Dihydro-9,10-ethano-anthracen-11,12-trans-dicarbonsaeure 
• 108-05-4 vinyl acetate 
• 5445-55-6 trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethano-anthracene 
• 108-21-4 Isopropyl acetate 

Downstream Products

• 23242-48-0 (+/-)-trans-11,12-bis-(toluene-4-sulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracene 
• 106750-89-4 trans-11,12-dichloromethyl-9,10-dihydro-9,10-ethanoanthracene 
• 88929-24-2 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 
• 41063-85-8 11R,12R-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 
• 88873-79-4 11R,12R-Bis-(diphenylphosphinomethyl)-9,10-ethano-perhydro-anthracen 
• 88873-78-3 11R,12R-Bis-(p-toluensulfonyloxymethyl)-9,10-ethano-perhydro-anthracen 
• 5445-55-6 (S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene 

Relevant articles and documents

Synthesis and antiproliferative action of a novel series of maprotiline analogues

The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymp

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels-Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels-Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers.

Asymmetric cycloaddition routes to both enantiomers of trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid

Fumarates prepared from a series of optically active alcohols were used as dienophiles in Lewis acid catalyzed asymmetric cycloadditions to anthracene. The reactions gave high yields and d.e.'s of the diester cycloaddition products and acid hydrolysis could be performed under conditions yielding only about 10% racemization. The reactions form a valuable synthetic pathway to both enantiomers of the bicyclic dicarboxylic acid, since di-(-)-menthyl fumarate yielded the (-)-(S,S)-enantiomer and di-(+)-iso-menthyl fumarate the (+)-(R,R)-enantiomer of the acid. The other fumarates, obtained from (-)-borneol, (+)-fenchol and (-)-isopulegol, likewise gave the (-)-(S,S)-enantiomer of the acid. The absolute stereochemistry of the products was confirmed via a single crystal X-ray crystallographic structure determination of the brucine salt of the (-)-(S,S)-enantiomer.