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

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

Used in Pharmaceutical Industry:
9,10-Dihydro-9,10-phenanthrene diol is used as a pharmaceutical compound for its potential therapeutic applications. The expression is: 9,10-Dihydro-9,10-phenanthrene diol is used as a [pharmaceutical compound] for [potential therapeutic applications].
Used in Chemical Research:
In the field of chemical research, 9,10-dihydro-9,10-phenanthrene diol is used as a [research compound] for [studying its properties and potential applications in various chemical reactions and processes].
Used in Environmental Applications:
9,10-Dihydro-9,10-phenanthrene diol is used as an [environmental remediation agent] for [its role in the degradation process of phenanthrene and other related compounds, contributing to the reduction of environmental pollution].
Used in Material Science:
In material science, 9,10-dihydro-9,10-phenanthrene diol is used as a [chemical building block] for [its potential use in the synthesis of new materials with specific properties, such as improved stability or enhanced functionality].

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

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

Downstream Products

• 484-17-3 9-Phenanthrol 
• 1210-05-5 Biphenyl-2,2'-dicarbaldehyde 
• 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 

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".

Hyperaromatic stabilization of arenium ions

Benzene-cis- and trans-1,2-dihydrodiols undergo acid-catalyzed dehydration at remarkably different rates: kcis/ktrans = 4500. This is explained by formation of a β-hydroxycarbocation intermediate in different initial conformations, one of which is stabilized by hyperconjugation amplified by an aromatic no-bond resonance structure (HOC6H6 + HOC6H5 H+). MP2 calculations and an unfavorable effect of benzoannelation on benzenium ion stability, implied by pKR measurements of -2.3, -8.0, and -11.9 for benzenium, 1-naphthalenium, and 9-phenanthrenium ions, respectively, support the explanation.

Photochemical oxidation of phenanthrene sorbed on silica gel

There have been relatively few detailed studies of PAH photochemical degradation mechanisms and products at solid/air interfaces under controlled conditions. Results from mechanistic studies on particulate simulants are important in understanding the fates of PAH sorbed on similar materials in natural settings. In this study, the photolysis of phenanthrene (PH) on silica gel, in the presence of air, has been carefully examined. Once sorbed onto the silica surface, PH is not observed to repartition into the gas phase, even under vacuum, and dark reactions of PH are not observed at the silica/air interface. Photolysis (254 nm) of PH leads to the formation of 2,2'-biformylbiphenyl (1), 9,10-phenanthrenequinone (2), cis-9,10-dihydrodihydroxyphenanthrene (3), benzocoumarin (4), 2,2'-biphenyldicarboxylic acid (5), 2-formyl-2'-biphenylcarboxylic acid (5), 2-formylbiphenyl (7),1,2-naphthalenedicarboxylic acid (8), and phthalic acid (9). These products account for 85-90% of the reacted PH. The photoproducts are independent of excitation wavelength (254 and 350 nm), and the reaction proceeds entirely through an initial step involving the addition of singlet molecular oxygen to the ground state of phenanthrene with subsequent thermal and/or photochemical reactions of the initially formed product. Singlet molecular oxygen is produced through quenching of the lowest triplet state of PH at the silica gel/air interface. The high material balance and detailed mechanistic information provided by this study serve as a standard for comparisons with the products and mechanism of PH photochemical oxidation on environmentally derived inorganic oxide particulates.