484-17-3

Basic information

• Product Name: 9-PHENANTHROL
• Synonyms: PHENANTHRENE-9-HYDROXY;9-HYDROXYPHENANTHRENE;9-PHENANTHROL;phenanthren-9-ol;9-PHENANTHROL, TECH.;9-Phenanthrenol;NSC 50554;9-Phenanthrol,60%,tech.
• CAS NO: 484-17-3
• Molecular Formula: C₁₄H₁₀O
• Molecular Weight: 194.23
• EINECS: 207-602-4
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 484-17-3.mol
• Article Data: 43

Chemical Properties

• Melting Point: 139-143 °C(lit.)
• Boiling Point: 290.68°C (rough estimate)
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.0550 (rough estimate)
• Vapor Pressure: 4.02E-07mmHg at 25°C
• Refractive Index: 1.5920 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.40±0.30(Predicted)
• CAS DataBase Reference: 9-PHENANTHROL(CAS DataBase Reference)
• NIST Chemistry Reference: 9-PHENANTHROL(484-17-3)
• EPA Substance Registry System: 9-PHENANTHROL(484-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: SF8288000
• Hazardous Substances Data: 484-17-3(Hazardous Substances Data)

Usage

Description

9-PHENANTHROL, also known as a metabolite of Phenanthrene, is a phenanthrol that is phenanthrene in which a hydrogen attached to a carbon in the central ring has been replaced by a hydroxy group. It is characterized by its brown powder appearance and is used in various applications due to its unique chemical properties.

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

• 5423-69-8 10-chloro-[9]phenanthrol 
• 2510-71-6 cis-9,10-dihydroxy-9,10-dihydrophenanthrene 
• 38399-63-2 2'-carboxybiphenyl-2-acetic acid 
• 4120-76-7 9-bromo-10-hydroxyphenanthrene 
• 5412-84-0 9,10-dihydro-10,10-dichlorophenanthren-9-one 
• 71112-64-6 9-phenanthrylmagnesium bromide 
• 84-11-7 9,10-phenanthrenequinone 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 5085-74-5 9-methoxyphenanthrene 
• 97833-08-4 (10-oxo-10H-[9]phenanthrylidene)-carbazic acid ethyl ester 
• 33070-58-5 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide 
• 85-01-8 phenanthrene 
• 67-56-1 methanol 

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 
• 215-29-2 1,2,3,4,6,7-Tribenzophenazin 
• 855877-02-0 salicylic acid-[9]phenanthryl ester 
• 84-11-7 9,10-phenanthrenequinone 
• 14140-04-6 cis-9,10-phenanthrenedione 9-oxime 
• 32281-40-6 9-hydroxy-10-nitrophenanthrene 
• 51417-63-1 1-fluoronaphthalen-2-ol 
• 59830-28-3 9,9-difluoro-10-keto-9,10-dihydrophenanthrene 
• 61708-78-9 2,2-diphenyl-2H-phrnanthro[9,10-e]pyran 

Relevant articles and documents

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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.

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.