2531-84-2

Usage

Uses

Used in Environmental Monitoring:
2-Methylphenanthrene is used as a biomarker for the presence of PAHs in the environment, particularly in areas where polystyrene plastic is commonly used or discarded. Its detection in environmental samples can indicate the presence of other potentially harmful PAHs, allowing for better monitoring and management of pollution.
Used in Chemical Research:
As a PAH, 2-Methylphenanthrene is used in chemical research to study the properties and behavior of PAHs in general. This research can help in understanding the environmental impact of PAHs, their potential health effects, and the development of methods for their detection and removal.
Used in Analytical Chemistry:
2-Methylphenanthrene is used as a reference compound in analytical chemistry for the calibration of instruments and methods used to detect and quantify PAHs. Its well-defined chemical structure and properties make it an ideal candidate for such applications.
Used in Plastics Industry:
Although 2-Methylphenanthrene is a pollutant in polystyrene plastic, it can also be used in the development of new materials and additives to improve the environmental performance of plastics. Research into its properties and interactions with other compounds can lead to the creation of more sustainable and eco-friendly plastic products.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 2-METHYLPHENANTHRENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. 2-METHYLPHENANTHRENE may be sensitive to prolonged exposure to light.

Fire Hazard

Flash point data for 2-METHYLPHENANTHRENE are not available. 2-METHYLPHENANTHRENE is probably combustible.

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

Upstream product

• 1504-28-5 7-methyl-2,3-dihydro-1H-phenanthren-4-one 
• 97277-93-5 2,2-dimethyl-1,2,3,4-tetrahydrophenanthrene 
• 88279-02-1 3-methyl-1-phenethyl-cyclohexanol 
• 858857-14-4 2-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene 
• 168777-08-0 1-hydroxy-3-methylphenanthrene 
• 15160-76-6 C₁₅H₁₃Br 
• 14064-48-3 3-methyl-stilbene 
• 77953-59-4 4,4-dimethylsulfanyl-2-butanone 
• 127543-80-0 (naphthalen-1-yl)methylmagnesium bromide 
• 122950-65-6 trans-2-methoxy-5-methylstilbene 
• 832-69-9 1-methylphenanthrene 
• 917-64-6 methyl magnesium iodide 
• 832-71-3 3-methylphenathrene 
• 883-20-5 9-methylphenanthrene 

Downstream Products

• 1217-45-4 9,10-dicyanoanthracene radical anion 
• 80721-78-4 2,6,9,10-tetracyanoanthracene radical anion 
• 832-69-9 1-methylphenanthrene 
• 832-71-3 3-methylphenathrene 
• 883-20-5 9-methylphenanthrene 
• 85-01-8 phenanthrene 
• 2606-54-4 2-phenanthrylmethanol 

Relevant academic research and scientific papers

Hydrous pyrolysis of methylphenanthrenes - Degradation and isomerization

A simulation of the chemical transformations of methylphenanthrenes in sediment was performed using hydrous pyrolysis technique. The results indicate that isomerization is not the primary cause of the change in the MPI1 index. Rather, the degradation reaction of methylphenanthrenes to phenanthrene is one of the most likely causes reversing the trend of the MPI1 index with increasing the heating temperature. An unusual isomerization between 2-methylphenanthrene and 9-methylphenanthrene was also observed during the course of heating experiments. A plausible mechanism involving [1,5]-methyl shift was proposed for this isomerization reaction.

A new parameter for maturity determination of organic matter in sediments based on the clay-catalyzed thermal isomerization of monomethylphenanthrenes

Monomethylphenanthrenes (MPs) were isomerized by heating in the presence of Na-montmorillonite at 250 - 400 °C. Isomerization between 1- and 2-MP was found to proceed faster than those between the other sets of MPs. On the basis of this facile interconversion, the molar ratio of 1- to 2-MP was suggested to be a useful new parameter for the maturity assessment of sedimentary organic matter. This parameter was tested in a geochemical study on Miocene to Pliocene sediments in the Shinjo basin of Yamagata Prefecture. We determined the molar ratio in 12 depth-differing sediments, and found an almost linearly decreasing trend in the ratio with increasing depth, showing a good correlation of this parameter to the maturity of the sedimentary organic matter.

A New Parameter for Maturity Assessment of Organic Materials in Sediments Based on Thermal Isomerization of Monomethylphenanthrenes

Monomethylphenanthrenes(MPs) were isomerized by heating in the presence of Na-montmorillonite to give a mixture of four isomers (1-, 2-, 3-, and 9-MP).The ratio of 1- and 2-MP produced from each isomer reached a constant value after appropriate time of heating.The ratio provides a new parameter for maturity assessment of sedimentary organic materials.

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.

Au-Cavitands: Size governed arene-alkyne cycloisomerization

With an inwardly directed reactive center and a well-defined binding pocket, Au(I) functionalized resorcin[4]arene cavitands have been shown to catalyze molecular transformations. The reactivity profiles that emerge differ from other Au(I) catalysts. The added constraint of a binding pocket gives rise to the possibility that the substrates might have to fit into the resorcinarene pocket; our hypothesis is that substrates that match the available space have different reaction outcomes than those that do not. Herein we report on the intramolecular cyclization of alkyne-aromatic substrates with variable alkynes and aromatic composition. We see that scaffold size most drastically dictates reactivity, especially when the substrate's features are particularly designed. The results of these experiments add to the veritable goldmine of information about the selectivity in catalysis that cavitands offer.

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.

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.

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.

Intramolecular carbonyl-ene reactions in the synthesis of peri-oxygenated hydroaromatics

2-Methallyl aromatic aldehydes, synthesized by Suzuki coupling of 2-formylphenylboronic acids, are shown to provide cycloalkylidene ene products under acidic conditions. Susceptibility of the products to aromatization is manoeuvred by varying the reaction conditions and catalysts including binol-derived Br?nsted acid catalysts. A peri-effect is identified as a controlling factor for the aromatizations. Several oxidative transformations of an ene product are carried out as model studies of hydroaromatic polyketide natural products.