2510-71-6

Basic information

• Product Name: 9,10-DIHYDRO-9,10-PHENANTHRENEDIOL
• Synonyms: AURORA KA-7081;9,10-DIHYDRO-9,10-PHENANTHRENEDIOL;(9R)-9,10-Dihydrophenanthrene-9,10β-diol;(9R,10S)-9,10-Dihydro-9,10-phenanthrenediol;(9R,10S)-9,10-Dihydrophenanthrene-9,10-diol;(Z)-9,10-Dihydroxy-9,10-dihydrophenanthrene;9,10-Dihydro-9,10-phenanthrenediol (Z)-;9,10-Phenanthrenediol, 9,10-dihydro- (Z)-
• CAS NO: 2510-71-6
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Mutagenesis Research Chemicals;Pharmaceuticals
• Mol File: 2510-71-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: 200.5°C
• Appearance: /
• Density: 1.326g/cm³
• Vapor Pressure: 2.85E-07mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: 9,10-DIHYDRO-9,10-PHENANTHRENEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DIHYDRO-9,10-PHENANTHRENEDIOL(2510-71-6)
• EPA Substance Registry System: 9,10-DIHYDRO-9,10-PHENANTHRENEDIOL(2510-71-6)

Safety Data

• Hazardous Substances Data: 2510-71-6(Hazardous Substances Data)

Usage

Uses

A dihydroxy metabolite of Phenanthrene with cis conformation. Produced via degradation by phenoloxidases and dioxygenases of Polyporus sp. S133.

InChI:InChI=1/C14H12O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8,13-16H

Upstream product

• 85-01-8 phenanthrene 
• 56-23-5 tetrachloromethane 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 969-93-7 cis-9.10-Diacetoxy-9.10-dihydro-phenanthren 
• 2005-10-9 6H-benzo[c]chromen-6-one 
• 863305-32-2 diphenic acid 
• 84-11-7 9,10-phenanthrenequinone 
• 1210-05-5 Biphenyl-2,2'-dicarbaldehyde 
• 484-17-3 9-Phenanthrol 

Relevant articles and documents

Hyperaromatic stabilization of arenium ions: A remarkable cis stereoselectivity of nucleophilic trapping of β-hydroxyarenium ions by water

Cis- and trans-1,2-dihydrodiol isomers of benzene undergo acid-catalyzed dehydration to form phenol. In principle the isomeric substrates react through a common β-hydroxybenzenium (cyclohexadienyl) carbocation. Notwithstanding, the isomers show a large difference in reactivity, kcis/k trans = 4500. This difference is reduced to kcis/k trans = 440 and 50 for the 1,2-dihydrodiols of naphthalene and 9,10-dihydrodiols of phenanthrene, respectively, and to 6.9 for the dihydrodiols of the nonaromatic 7,8-double bond of acenaphthylene. Because the difference in stabilities of cis- and trans-dihydrodiols should be no more than 2-3-fold, these results imply a high cis stereoselectivity for nucleophilic trapping of a β-hydroxyarenium cation by water in the reverse of the carbocation-forming reaction. This is confirmed by studies of the 10-hydroxy-9-phenanthrenium ion generated from aqueous solvolyses of the trans-9,10-bromohydrin derivative of phenanthrene and the monotrichloroacetate ester of the phenanthrene cis-9,10-dihydrodiol. The cis stereoselectivity of forward and reverse reactions is explained by the formation (in the "forward" reaction) of different conformations of carbocation from cis- and trans-dihydrodiol reactants with respectively β-C-H and β-C-OH bonds in pseudoaxial positions with respect to the charge center of the carbocation optimal for hyperconjugation. Formation of different conformations is constrained by departure of the (protonated) OH leaving group from a pseudoaxial position. The difference in stability of the carbocations is suggested to stem (a) from the greater hyperconjugative ability of a C-H than a C-OH bond and (b) from enhanced conjugation arising from the stabilizing influence of an aromatic ring in the no-bond resonance structures representing the hyperconjugation (C 6H6OH+ ? C6H5OH H+). This is consistent with an earlier suggestion by Mulliken and a demonstration by Schleyer that the benzenium ion is subject to hyperconjugative aromatic stabilization. It is proposed that, in analogy with the terms homoconjugation and homoaromaticity, arenium ions should be considered as "hyperaromatic".

A novel Nickel(0)-mediated one-pot cascade reaction to cis-9,10- dihydroxy-9,10-dihydrophenanthrenes and 9-phenanthrones

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