66267-18-3

Basic information

• Product Name: (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol
• Synonyms: trans-1,2-dihydroxy-1,2-dihydrobenzo(a,h)anthracene
• CAS NO: 66267-18-3
• Molecular Formula: C₂₂H₁₆O₂
• Molecular Weight: 312.3612
• Mol File: 66267-18-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 606.1°C at 760 mmHg
• Flash Point: 289.5°C
• Density: 1.382g/cm³
• Vapor Pressure: 1.52E-15mmHg at 25°C
• Refractive Index: 1.831
• CAS DataBase Reference: (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol(66267-18-3)
• EPA Substance Registry System: (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol(66267-18-3)

Safety Data

• Hazardous Substances Data: 66267-18-3(Hazardous Substances Data)

Usage

Description

(1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol is a chiral tetraphene, a type of polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, with two hydroxyl groups attached to the rings. The (1S,2S) configuration denotes a specific arrangement of atoms around its stereocenter, which is crucial for its properties and potential applications.

Uses

Used in Organic Electronics:
(1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol is used as a component in organic light-emitting diodes (OLEDs) for its aromatic properties that contribute to the device's light-emitting capabilities.
Used in Organic Photovoltaic Cells:
In the field of organic photovoltaics, (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol serves as a material that can enhance the efficiency of solar cells by improving charge transport and light absorption.
Used in Medicinal Chemistry:
(1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol is utilized as a starting material or intermediate in the synthesis of new drugs, taking advantage of its chiral center and aromatic structure to create bioactive compounds.
Environmental Concerns:
While (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol has potential applications in various fields, it is also a PAH derivative, which means it may have environmental implications due to its potential toxicity and carcinogenicity. Proper handling and disposal are necessary to mitigate any adverse effects on the environment.

Upstream product

• 72378-83-7 1,4,7,8,11,14-Hexahydrodibenzanthracene 
• 57816-08-7 7,14-dihydrodibenz[a,h]anthracene 
• 66267-13-8 trans-1,2-bis(benzoyloxy)-1,2,3,4-tetrahydrodibenzanthracene 
• 79970-90-4 C₃₆H₂₅BrO₄ 
• 79970-86-8 1-acetoxy-1,2,3,4-tetrahydrodibenzanthracene 
• 79970-88-0 3,4-dihydrodibenzanthracene 
• 72390-46-6 1,2,3,4,7,8,9,10,11,14-decahydro-dibenz[a,h]anthracene 
• 153-39-9 1,2,3,4-tetrahydrodibenzanthracene 
• 53-70-3 dibenzo[a,h]anthracene 
• 66267-08-1 1,2-dihydrodibenzanthracen-4(3H)-one 
• 66302-72-5 trans-1,2-bis(benzoyloxy)-1,2-dihydrodibenzanthracene 
• 66267-18-3 trans-1,2-dihydroxy-1,2-dihydrodibenzanthracene 

Downstream Products

• 1421-82-5 (-)-(1R,2R)-1,2-dihydroxy-1,2-dihydrodibenz[a,h]anthracene 
• 79036-79-6 (1S,2R,3R,4R)-1,2,3,4-Tetrahydro-dibenzo[a,h]anthracene-1,2,3,4-tetraol 
• 79036-79-6 (1S,2R,3S,4R)-1,2,3,4-Tetrahydro-dibenzo[a,h]anthracene-1,2,3,4-tetraol 
• 79036-79-6 (1S,2R,3R,4S)-1,2,3,4-Tetrahydro-dibenzo[a,h]anthracene-1,2,3,4-tetraol 

Relevant articles and documents

Synthesis, absolute configuration, and bacterial mutagenicity of the 8 stereoisomeric vicinal diol epoxides at the terminal benzo ring of carcinogenic dibenz[ a,h ]anthracene

The synthesis of the 8 possible stereoisomeric diol epoxides (DEs) at the terminal benzo ring of carcinogenic dibenz[a,h]anthracene (DBA) is reported. trans-3,4-Dihydroxy-3,4-dihydro-DBA (1) afforded the 4 bay region DEs: the enantiomeric pairs of the ant

Synthesis of Biologically Active Metabolites of Dibenzanthracene

Syntheses are described of the trans 1,2- and 3,4-dihydro diol metabolites (3a and 1a) of dibenzanthracene (DBA) and the corresponding diol epoxide derivatives 4 and 2, implicated as the ultimate carcinogenic metabolites of DBA.The synheses of 1a and 3a are accomplished from DBA via lithium-ammonia reduction to 1,4,7,8,11,14-hexahydrodibenzanthracene, base-catalyzed isomerization, Prevost reaction, dehydrogenation, and basic methanolysis.This approach involves considerably fewer steps and affords superior overall yields than obtainable by more conventional methods entailing multistep ring construction.Epoxidation of 1a affords stereospecifically the anti diol epoxide isomer 2, whereas similar reaction of 3a furnishes a mixture of the corresponding syn and anti diol epoxide isomers in 3:1 ratio.Biological evidence implicates 1a and 2 as proximate and ultimate carcinogenic forms, respectively, of DBA.Synthesis of 3-hydroxydibenzanthracene, also known to be a metabolite of DBA, is also described.