832-64-4

Usage

Uses

Used in Chemical Synthesis:
4-Methylphenanthrene is used as a chemical intermediate for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Its unique structure allows for selective functionalization and modification, making it a valuable building block in organic chemistry.
Used in Environmental Research:
As a derivative of phenanthrene, 4-methylphenanthrene is used in environmental research to study the behavior, fate, and transport of PAHs in the environment. Understanding the properties and effects of these compounds is crucial for assessing their impact on ecosystems and human health.
Used in Analytical Chemistry:
4-Methylphenanthrene is employed as a reference compound in analytical chemistry for the development and validation of analytical methods, such as chromatography and mass spectrometry. Its distinct chemical properties make it suitable for evaluating the performance of these techniques in detecting and quantifying PAHs and their derivatives.
Used in Material Science:
4-Methylphenanthrene has potential applications in material science, particularly in the development of advanced materials with unique optical, electronic, and thermal properties. Its molecular structure can be utilized to design and synthesize novel materials with specific characteristics for various applications, such as sensors, energy storage, and optoelectronics.

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

Upstream product

• 855615-39-3 4-methyl-phenanthrene-1,2-dicarboxylic acid-anhydride 
• 77536-58-4 1,2,3,4-tetrahydro-4-methyl-4-phenanthrenol 
• 122950-68-9 trans-2-methoxy-3-methylstilbene 
• 74585-27-6 4-methyl-phenanthrene-9,10-dicarboxylic anhydride 
• 78396-22-2 4-Naphthalen-1-yl-pentan-1-ol 
• 65810-08-4 (2-Hydroxy-2-methylcyclohexane)-(5',6',7',8'-tetrahydrochroman)-spirane-(1,2') 
• 74585-28-7 4-methyl-9,10-phenanthryne 
• 15016-42-9 2-vinylbenzeneboronic acid 
• 3354-58-3 2-allyl-6-methylphenol 
• 95-48-7 ortho-cresol 
• 119-64-2 tetralin 
• 854678-24-3 4-oxo-4-(5,6,7,8-tetrahydro-[2]naphthyl)-butyric acid methyl ester 
• 27343-41-5 4-[1]naphthyl-valeric acid 
• 78396-21-1 4-Naphthalen-1-yl-pentanenitrile 

Downstream Products

• 203-64-5 4H-Cyclopenta[def]phenanthrene 
• 41498-43-5 4-Phenanthrencarbaldehyd 
• 832-71-3 3-methylphenathrene 
• 85-01-8 phenanthrene 
• 22863-79-2 4‐phenanthrenemethanol 

Relevant academic research and scientific papers

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons

A catalytic, metal-free and chemoselective oxidative intramolecular coupling of arene and alkene C?H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta-chloroperoxybenzoic acid (m-CPBA), reacts with o-vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.

Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.

Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.

Polycationic ligands in gold catalysis: Synthesis and applications of extremely π-acidic catalysts

Very often ligands are anionic or neutral species. Cationic ones are rare, and, when used, the positively charged groups are normally appended to the periphery of the ligand. Here, we describe a dicationic phosphine with no spacer between the phosphorus atom and the two positively charged groups. This structural feature makes its donor ability poorer than that of phosphites and only comparable to extremely toxic or pyrophoric compounds such as PF 3 or P(CF3)3. By exploiting these properties, a new Au catalyst has been developed displaying a dramatically enhanced capacity to activate π-systems. This has been used to synthesize very sterically hindered and naturally occurring 4,5-disubstituted phenanthrenes. The present approach is expected to be applicable to the development and improvement of many other transition metal catalyzed transformations that benefit from extremely strong π-acceptor ligands. The mechanism of selected catalytic transformations has been explored by density functional calculations.

Synthesis of phenanthrenes by cationic chromium(III) porphyrin-catalyzed dehydration cycloaromatization

Readily available biphenyl derivatives with ortho oxirane moiety react in the presence of cationic chromiun(III) porphyrin catalyst to afford phenanthrenes. The reaction is considered to be triggered by activation of the oxirane moiety through coordination to the Lewis acidic cationic chromium to give aldehyde via 1,2-hydride shift, which reacts with arene through intramolecular electrophilic aromatic substitution and subsequent dehydration. The reaction allows constructing a variety of polycyclic aromatic and heteroaromatic compounds.

Straightforward synthesis of phenanthrenes from styrenes and arenes

Semi-one-pot synthesis of phenanthrenes from styrenes and arenes was developed through cross-dehydrogenative coupling. A sequence of Heck-type coupling and photo-cyclization were involved and a variety of functionalities were tolerated. This method provides an effective and practical protocol towards the synthesis of substituted phenanthrenes. The Royal Society of Chemistry 2012.

Synthesis of phenanthrene and alkyl phenanthrenes by palladium(0)-catalyzed pericyclic reactions

Palladium-catalyzed pericyclic reactions have been developed for the synthesis of phenanthrenes. This method is also useful for the synthesis of monoalkyl and dialkyl phenanthrene derivatives. Georg Thieme Verlag Stuttgart.

Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes

The isoquinolinone hemisphere of Sch 56036 has been prepared using a modified Pomeranz-Fritsch reaction and the synthesis of the phenanthrene core has been modelled via a Suzuki coupling and subsequent ring closing metathesis.