484-17-3

Usage

Uses

Used in Chemical Research:
9-PHENANTHROL is used as a research compound for investigating C K-edge and O K-edge near-edge X-ray absorption fine structure (NEXAFS) spectra of single-wall carbon nanotubes. This application helps in understanding the interactions and properties of these materials at a molecular level.
Used in Pharmaceutical Industry:
As a metabolite of Phenanthrene, 9-PHENANTHROL is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Material Science:
9-PHENANTHROL, due to its brown powder form, can be used in the development of new materials or as an additive in the material science industry. Its specific properties may contribute to the enhancement of certain material characteristics, such as stability or reactivity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 86, 1959 DOI: 10.1021/jo01083a025Tetrahedron Letters, 29, p. 5459, 1988 DOI: 10.1016/S0040-4039(00)80786-8

Biochem/physiol Actions

9-Phenanthrol is inhibitor of the transient receptor potential melastatin 4 (TRPM) channel, a Ca2+ -activated non-selective cation channel.

InChI:InChI=1/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H

Upstream product

• 2510-71-6 cis-9,10-dihydroxy-9,10-dihydrophenanthrene 
• 84-11-7 9,10-phenanthrenequinone 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 585-08-0 phenanthrene-9,10-oxide 
• 486-25-9 9-fluorenone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 776-35-2 9,10-dihydrophenanthrene 
• 484-16-2 10H-phenanthren-9-one 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 3112-05-8 1-biphenyl-2-yl-2-diazo-ethanone 
• 573-17-1 9-bromophenanthrene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 36368-33-9 10-benzeneazo-9-phenanthrol 
• 85-01-8 phenanthrene 
• 5325-97-3 1,2,3,4,5,6,7,8-Octahydrophenanthrene 
• 947-73-9 9-Aminophenanthrene 
• 16269-40-2 N-9-phenanthrenyl-9-phenanthrenamine 
• 957-82-4 9-Acetoxy-phenanthren 
• 64330-55-8 phenanthro[9,10-d][1,3]oxazol-2-yl-phenylmethanone 
• 21639-88-3 2-methylphenanthro[9,10-d][1,3]oxazole 
• 4410-14-4 2-phenylphenanthro[9,10-d]oxazole 
• 120270-55-5 N,N-diethyl 10-(4'-nitrophenyl)phenanthren-9-yl-O-carbamate 
• 1574190-78-5 2-hydroxy-2-phenylphenanthro[9,10-b]furan-3(2H)-one 
• 883-20-5 9-methylphenanthrene 
• 81269-64-9 3-phenylphenanthro[9,10-b]furan-2(3H)-one 

Relevant academic research and scientific papers

A simple Hückel model-driven strategy to overcome electronic barriers to retro-Brook silylation relevant to aryne and bisaryne precursor synthesis

ortho-Silylaryl triflate precursors (oSATs) have been responsible for many recent advances in aryne chemistry and are most commonly accessed from the corresponding 2-bromophenol. A retro-BrookO- toC-silyl transfer is a key step in this synthesis but not all aromatic species are amenable to the transformation, with no functionalized bisbenzyneoSATs reported. Simple Hückel models are presented which show that the calculated aromaticity at the brominated position is an accurate predictor of successful retro-Brook reaction, validated synthetically by a new success and a predicted failure. From this, the synthesis of a novel difunctionalized bisaryne precursor has been tested, requiring different approaches to install the twoC-silyl groups. The first successful use of a disubstitutedo-silylaryl sulfonate bisbenzyne precursor in Diels-Alder reactions is then shown.

Preparation method of 9-hydroxyphenanthrene

The invention discloses a preparation method of 9-hydroxyphenanthrene, the preparation method comprises the following steps: taking a phenanthrene solution as a raw material, carrying out bromination, methoxylation and demethylation reaction to obtain the 9-hydroxyphenanthrene. The preparation method has the advantages of low preparation cost, high preparation efficiency, environmental friendliness, greatly improved product yield and high quality of the prepared product, is suitable for industrial production, and can be used for large-scale industrial preparation of 9-hydroxyphenanthrene and derivatives thereof.

Thermodynamically Stable o-Quinodimethane: Synthesis, Structure, and Reactivity

Thermal isomerization of cyclobutaphenanthrene to o-quinodimethane was investigated. Sterically congested substituents or electron-donating substituents on the four-membered ring promoted the ring-opening, affording o-quinodimethane in a relatively stable form. Isolation of the newly prepared o-quinodimethane allowed its structural elucidation and investigation of its potential reactivities. Dual [4+2] cycloaddition of an aryne and o-quinodimethane afforded tetrabenzopentacene, demonstrating the synthetic application of the isolated compound.

ELECTROACTIVE COMPOUNDS

There is provided a compound having Formula (I) In Formula I = Ar1 is a hydrocarbon aryl group, a heteroaryl group, or a substituted derivative thereof; and Q has Formula (Q1), (Q2), or (Q3) The variables are described in detail herein.

β-Diketone boron difluoride dye-functionalized conjugated microporous polymers for efficient aerobic oxidative photocatalysis

Incorporation of organic chromophores into conjugated micro/mesoporous polymers (CMPs) provides a promising avenue for developing recyclable heterogeneous photocatalysts by overcoming tedious separation and low reusability of homogeneous organic dye-based photocatalysts. However, the design principle and the underlying structure-property relationship for fabricating and selecting various organic dye-embedded CMPs for efficient photocatalysis have not been well-constructed so far. In this study, we described the rational fabrication of two new CMPsviathe one-step Sonogashira coupling using β-diketone boron difluoride dye as the key linker and commonly used building blocks (triphenylamine/triphenylbenzene) as the cores. The resulting boron-dye containing CMPs were efficiently employed as the metal-free photocatalysts in two typical aerobic oxidative organic transformations including coupling of benzylamine and oxidation of aryl boronic acids to corresponding aryl phenols, which have never been explored with other boron-dye-embedded CMPs. They exhibited superior photocatalytic performance compared to their boron-free counterparts due to their wide visible-light absorption, narrow optical bandgaps, and extended π-conjugation due to boron-complexation. The present study establishes β-diketone boron difluoride dyes as efficient building blocks for fabricating new CMP-based photocatalysts.

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid

Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.

Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis

Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.

Hydroxyl-substituted phenanthrene derivative synthesis method

The invention relates to a hydroxyl-substituted phenanthrene derivative synthesis method, which includes taking a 2-carboxymethyl biphenyl compound as a raw material; and reacting under the action ofa catalyst to obtain a hydroxyl-substituted phenanthrene derivative, wherein the catalyst comprises one or two of trifluoromethanesulfonic acid or phosphorus pentoxide. Compared with the prior art, the synthesis method has the advantages of the cheap and easily-available catalyst, good universality of functional groups, simple and convenient operation, short reaction time, high reaction yield, mild reaction conditions and the like.

Synthesis method of 9-hydroxyphenanthrene and derivatives thereof

The invention discloses a synthesis method of 9-hydroxyphenanthrene and derivatives thereof, and belongs to the technical field of organic synthesis. The reaction activities of multiple trivalent iodine reagents in different mediums are researched; provided is a method for directly conversing a 9-site C-H bond of iodobenzene diacetate, iodobenzene bis(trifluoroacetate), or phenanthrene into a C-Obond through iodobenzene diacetate, iodobenzene bis(trifluoroacetate), or iodosobenzene under an acidic condition, and then the intermediate is converted into 9-hydroxyphenanthrene under an alkaline reduction condition. A novel method is provided for synthesizing 9-hydroxyphenanthrene. A novel method is provided for massive conversion of cheap phenanthrene polycyclic aromatic hydrocarbons. The synthesis method is suitable for industrial production and the additional value of phenanthrene polycyclic aromatic hydrocarbons is greatly increased. The yield of 9-hydroxyphenanthrene is 78 to 90%; theyield of corresponding esters and ethers is 80 to 95%; the product structure is confirmed by NMR spectrums, and the product purity is greater than 99%.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.