1576-67-6

Usage

Uses

Used in Environmental and Analytical Chemistry:
3,6-Dimethylphenanthrene is used as a reference standard for studying PAHs and their impact on the environment. It helps in understanding the behavior, distribution, and potential health hazards of PAHs in various environmental matrices.
Used in Organic Electronics:
Due to its compact structure and high stability, 3,6-Dimethylphenanthrene is being investigated for its potential use in organic electronics. Its properties make it a promising candidate for applications in electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs).
Used in Regulatory Controls:
3,6-Dimethylphenanthrene is subject to regulatory controls to limit its release into the environment. These controls aim to minimize the potential health hazards associated with PAHs and protect both human health and the environment from their adverse effects.

Upstream product

• 18869-29-9 (E)-4,4'-dimethylstilbene 
• 13250-88-9 bis(4-methylbenzyl)sulfane 
• 2510-76-1 (Z)-4,4'-dimethylstilbene 
• 108-31-6 maleic anhydride 
• 80654-95-1 5,5'-dimethyl-1:1'-bicyclohexenyl 
• 856645-46-0 3,3'-Dimethyl-8,9-benzo-spiro<5.5>undecan 
• 765-43-5 Cyclopropyl methyl ketone 
• 872-75-3 1-(2,2-dimethyl-cyclopropyl)-ethanone 
• 14114-01-3 cyclobutyl cyclopropyl ketone 
• 1121-37-5 dicyclopropyl ketone 
• 339560-50-8 10-Oxo-3,3'-dimethyl-8,9-benzo-spiro<5.5>undecan 
• 96979-13-4 2,2-(4-Methyl-cyclohexan)-4-(p-tolyl)-buttersaeure 
• 591-24-2 3-Methylcyclohexanone 
• 1588-49-4 4,4'-dimethylstilbene 

Downstream Products

• 93012-36-3 5,5'-dimethylbiphenyl-2,2'-dicarboxylic acid 
• 1217-45-4 9,10-dicyanoanthracene radical anion 
• 80721-78-4 2,6,9,10-tetracyanoanthracene radical anion 
• 52988-30-4 3-((Z)-2-Biphenyl-4-yl-vinyl)-6-methyl-phenanthrene 
• 52988-33-7 3-((E)-2-Biphenyl-4-yl-vinyl)-6-methyl-phenanthrene 

Relevant academic research and scientific papers

Synthesis and characterisation of new nonracemic quaternary ammonium salts

New nonracemic monemeric and dimeric quaternary ammonium salts have been synthesized by the reaction of commercially available quinine with phenanthrene derivatives and fully characterized by IR, NMR spectroscopy and X-ray crystallographic analysis.

Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes

The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive (l)-(+)-tartaric acid and 4-methylstyrene is described. These helical structures were transformed into bis-iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre-catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.

Controlling photochemical geometric isomerization of a stilbene and dimerization of a styrene using a confined reaction cavity in water

Utility of a water-soluble deep cavity cavitand, octa acid, as a reaction medium is illustrated by carrying out photochemical reactions of a stilbene and a styrene included within the octa acid in water. Geometric isomerization of trans-4,4′-dimethyl stilbene is restricted while dimerization of 4-methyl styrene is facilitated within the octa acid cavity. The excited-state chemistry of both systems is different in this medium from that in organic solvents. The change in chemistry is attributed to the supramolecular effects provided by the host cavity.

Cyclopropylcarbinyl-type ring openings. Reconciling the chemistry of neutral radicals and radical anions

Cyclopropylcarbinyl → homoallyl and related rearrangements of radical ions (a) are frequently used as mechanistic "probes" to detect the occurrence of single electron transfer in chemical and biochemical processes, (b) provide the basis for mechanism-base

4,15-Diamino[2.2]paracyclophane as a starting material for pseudo-geminally substituted [2.2] paracyclophanes

Diazotization of the title compound 3, followed by treatment of the formed bis(diazonium ion) with cuprous chloride, yields the pseudo-geminal dichloride 1. Similarly, 3 is converted into the bis(azide) 5 when sodium azide is used as the trapping nucleophile. Hypochlorite oxidation of 3 furnishes the azo compound 4, the first multi-bridged cyclophane with a bridge consisting only of heteroatoms. Reduction of 4 with zinc/acetic acid affords the substrate 3 again. Treatment of 4 with bromine/iron powder or iodine monochloride causes deazotization accompanied by halogen introduction in pseudo-geminal position (i.e., formation of 2 and 6, respectively). Flash vacuum pyrolysis (450 °C, 0.01 Torr) of 4 produces the phenanthrene derivatives 13 and 14, while with tetracyanoethylene (TCNE) the azophane undergoes rapid cycloaddition at room temperature to give the [2+4] cycloadduct 16. The structures of 1, 2, 4-6, and 16 have been determined by X-ray structural analysis. Molecular packing patterns are determined by weak hydrogen bonds; a common packing pattern for cyclophane derivatives is ascribed to C-H...π interactions. Full bandshape analyses of the bridge proton signals in the 1H NMR spectra of 1, 2, 6, and of the difluoro analogue 17 yielded the vicinal 1H,1H coupling constants. These reflect the 1:1 equilibrium between the two skew conformations of the bridges. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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.

Synthesis and optoelectronic properties of some new thiahelicenes

(Chemical Equation Presented) New symmetrical helically chiral penta- and heptacyclic aromatic systems containing two thiophene rings have been prepared, in good yields, under mild conditions using a photochemical route. Optoelectronic properties of these helically aromatic thia-systems were determined and exhibit interesting behavior. Copyright Taylor & Francis Group, LLC.

Preparation of phenanthrenes by photocyclization of stilbenes containing a tosyl group on the central double bond. A versatile approach to the synthesis of phenanthrenes and phenanthrenoids

We have developed a useful modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.

Synthesis of the novel conjugated ω,ω′-diaryl/heteroaryl hexatriene system with the central double bond in a heteroaromatic ring: photochemical transformations of 2,3-divinylfuran derivatives

New β,β′-aryl/heteroaryl 2,3-divinylfuran derivatives (9a-d) in which a hexatriene system is a part of heteroaromatic ring have been synthesized and their photochemical properties were investigated. The primary process observed was the isomerization to trans,trans-isomers 9a-d followed by photochemical rearrangement of the furan ring giving the phototransposition products (I-IV). Stilbenes (20, 21) and phenanthrenes (22, 25, and 26), formed as secondary products from the competitive intermolecular cycloadditions, were also observed.

Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids

(Equation presented) The irradiation with UV light of a number of 1,2-diaryl-1-tosylstilbenes, in the presence of base, leads to the corresponding phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes.