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

General Description

The chemical compound (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol is a type of tetraphene, which is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings. The compound is in the form of a dihydroxy derivative, meaning it contains two hydroxyl groups attached to the benzene rings. (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol is a chiral molecule, with the (1S,2S) configuration indicating that it has a specific arrangement of atoms around its stereocenter. Due to its aromatic nature, tetraphene derivatives like (1S,2S)-1,2-dihydrobenzo[k]tetraphene-1,2-diol have potential applications in the field of organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, as well as in medicinal chemistry for the development of new drugs. However, like many PAHs and related compounds, tetraphenes are also of environmental concern due to their potential toxicity and carcinogenicity.

Upstream product

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

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.