883-20-5

Usage

Uses

9-Methylphenanthrene is used as a chemical intermediate in the synthesis of various organic compounds, particularly in the production of dyes, pharmaceuticals, and other specialty chemicals. Its unique structure and properties make it a valuable building block for the development of new molecules with specific applications.
Used in Chemical Synthesis Industry:
9-Methylphenanthrene is used as a chemical intermediate for the synthesis of dyes, pharmaceuticals, and other specialty chemicals due to its unique structure and properties.
Used in Environmental Research:
9-Methylphenanthrene is utilized in environmental research to study the behavior, fate, and transport of PAHs in the environment. Understanding its persistence, bioaccumulation, and potential impacts on ecosystems is crucial for developing strategies to mitigate its environmental hazards.
Used in Toxicology Studies:
9-Methylphenanthrene is employed in toxicology studies to investigate its potential carcinogenic and toxic effects on humans and animals. These studies help in understanding the mechanisms of action, dose-response relationships, and potential health risks associated with exposure to 9-Methylphenanthrene.
Used in Analytical Chemistry:
9-Methylphenanthrene is used as a reference compound in analytical chemistry for the development and validation of analytical methods for the detection and quantification of PAHs in various matrices, such as air, water, soil, and biological samples.

InChI:InChI=1/C15H12/c1-11-10-12-6-2-3-8-14(12)15-9-5-4-7-13(11)15/h2-10H,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 501680-77-9 1-biphenyl-2-yl-2-methoxy-ethanone 
• 1620-14-0 1-(diethylamino)propan-2-one 
• 23533-35-9 biphenyl-2-ylmagnesium iodide 
• 621-87-4 3-phenoxy-2-propanone 
• 5342-87-0 1,2-diphenylpropane-2-ol 
• 3952-36-1 2-(9H-fluoren-9-yl)ethanol 
• 27343-39-1 9-methyl-3,4-dihydrophenanthren-1(2H)-one 
• 951-05-3 9-(chloromethyl)phenanthrene 
• 22364-43-8 2-(prop-1-en-2-yl)-1,1'-biphenyl 
• 13662-06-1 1-(naphthalen-2-yloxy)propan-2-one 
• 219-92-1 dibenzocycloheptene 
• 3023-49-2 9-(1-hydroxyethyl)fluorene 
• 108837-39-4 1,2,3,4-tetrahydro-10-methylphenanthrene 

Downstream Products

• 215-95-2 Tetrabenzotetracen 
• 24471-57-6 9-bromomethylphenantrene 
• 67590-88-9 cis-1-(9-phenanthryl)-4-phenyl-1-buten-3-yne 
• 67590-89-0 trans-1-(9-phenanthryl)-4-phenyl-1-buten-3-yne 
• 2531-84-2 2-methylphenathrene 
• 832-69-9 1-methylphenanthrene 
• 832-71-3 3-methylphenathrene 
• 85-01-8 phenanthrene 
• 100914-80-5 2’acetyl-[1,1'-biphenyl]-2-carbaldehyde 
• 81568-57-2 phenanthrene-9,10-dicarboxylic acid 
• 81568-58-3 N-benzylideneaminophenanthrene-9,10-dicarboximide 
• 123-56-8 Succinimide 
• 95854-32-3 diethyl 9-phenantrylmethylphosphonate 
• 33895-28-2 9-Phenanthrylmethyl-triphenylphosphonium-bromid 

Relevant academic research and scientific papers

Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes

The application of a C(vinyl), C(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C(vinyl), C(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl C–H activation and dual decarboxylation sequence, forming phenanthrenes and cyclohepta[1,2,3-de]naphthalenes regioselectively in good yields. The synthetic versatility of this protocol is highlighted by the gram-scale synthesis and synthesizing functional material molecule.

Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst

Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Br?nsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.

A methylation platform of unconventional inert aryl electrophiles: Trimethylboroxine as a universal methylating reagent

Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread "inert"functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry.

Exhaustive Reduction of Esters Enabled by Nickel Catalysis

We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of -CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C-O bonds are demonstrated.

AuCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis

Compared with the ripeness of olefin metathesis, exploration of the construction of carbon–carbon double bonds through the catalytic carbonyl–olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl3-catalyzed intramolecular ring-closing carbonyl–olefin metathesis reaction is described. This method features easily accessible starting materials, simple operation, good functional-group tolerance and short reaction times, and provides the target cyclopentenes, polycycles, benzocarbocycles, and N-heterocycle derivatives in good to excellent yields.

Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions

A cobaloxime-catalyzed acceptorless dehydrogenative cyclization of o-teraryls was developed. In stark contrast to the established methods such as the Scholl or Mallory reactions, this method does not require any strong acids or oxidants, and shows high atom economy and a broad substrate scope. It operates at near room temperature with light as the source of energy. Acid- or oxidant-sensitive functional groups, such as 4-methoxyphenyl, unprotected benzyl alcohol, silyl ether, and thiophene groups are tolerated. Remarkably, aryls with electron-withdrawing groups, and electron-poor heteroarenes, such as pyridine and pyrimidine, can also react. Preliminary mechanistic study reveals that hydrogen gas is released during the reaction, and both light and the cobalt catalyst are important for the dehydrogenation step.

Preparation method of fused ring compound

The invention discloses a preparation method of a fused ring compound III. The preparation method comprises the following step: in a solvent and in the presence of palladium acetate, alkali and a ligand, carrying out a reaction shown in the specification on a compound I and a compound II to obtain a compound III. The preparation method disclosed by the invention is relatively good in compatibilitywith a substrate, various polycyclic aromatic hydrocarbon compounds can be simply obtained in a short period of time through convergent synthesis, and particularly, heteroatom-containing polycyclic aromatic hydrocarbon shows extremely excellent regioselectivity.

Sequential Cross-Coupling/Annulation of ortho-Vinyl Bromobenzenes with Aromatic Bromides for the Synthesis of Polycyclic Aromatic Compounds

A sequential cross-coupling/annulation of ortho-vinyl bromobenzenes with aromatic bromides was realized, providing a direct and modular approach to access polycyclic aromatic compounds. A vinyl-coordinated palladacycle was proposed as the key intermediate for this sequential process. Excellent chemoselectivity and regioselectivity were observed in this transformation. The practicability of this method is highlighted by its broad substrate scope, excellent functional group tolerance, and rich transformations associated with the obtained products.

Method for synthesizing 6-methyl phenanthridine compound

The present invention provides a method for synthesizing a 6-methyl phenanthridine compound. The method is as below: using a substituted azide terminal alkene compound represented by a formula I as astarting material, conducting a reaction in an organic solvent under the action of a copper catalyst and an oxidizing agent at 60 to 100 DEG C for 8 to 16 hours, and conducting post-treatment on the obtained reaction solution to obtain 6-methyl phenanthridine represented by a formula II and derivatives thereof, wherein the mass ratio of the substituted azide terminal alkene compound represented bythe formula I, the copper catalyst and the oxidizing agent is 1:(0.11-0.3):(1-3). The method of the present invention is safe and environmentally friendly, and does not generate waste water; the substrate has good adaptability and various substituents can be aromatized/methylated; the reaction conditions are mild, and the reaction can be carried out at a lower temperature; the raw materials do not need to be aromatized or methylated in advance; the reaction steps are simple; therefore, the method is a new route for synthesis of various 6-methyl phenanthridines containing substituents.

Carbonyl-Olefin Metathesis Catalyzed by Molecular Iodine

The carbonyl-olefin metathesis reaction could facilitate rapid functional group interconversion and allow construction of complicated organic structures. Herein, we demonstrate that elemental iodine, a very simple catalyst, can efficiently promote this chemical transformation under mild reaction conditions. Our mechanistic studies revealed intriguing aspects of the activation mode via molecular iodine and the iodonium ion that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.