16606-46-5

Usage

Chemical structure

Polycyclic aromatic hydrocarbon with a naphthalene core and a phenyl group attached to one of the carbon atoms.

Applications

a. Production of dyes
b. Production of pharmaceuticals
c. Synthesis of various organic compounds

Physical properties

a. Flammable liquid
b. High melting point

Chemical properties

a. Exhibits aromatic properties
b. Exhibits aliphatic properties

Safety concerns

a. Potential health hazards if not used properly
b. Importance of handling with care

InChI:InChI=1/C16H14/c1-2-7-13(8-3-1)16-12-6-10-14-9-4-5-11-15(14)16/h1-11,16H,12H2

Upstream product

• 545-87-9 1-phenyl-1,2-dihydro-[1]naphthoic acid 
• 100-42-5 styrene 
• 147506-92-1 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl 
• 79628-38-9 bis(1,2,3,4-tetrahydro-4-phenyl-1,1-naphthyl)diazene 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 
• 51751-10-1 4-Phenyl-1,2,3,4-tetrahydro-1-naphthol 
• 85803-90-3 exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene 
• 85803-90-3 endo-4-phenylbenzobicyclo<3.1.0>hex-2-ene 
• 82645-20-3 (1aS*,6aR*)-1a-phenyl-1,1a,6,6a-tetrahydrocyclopropa[a]indene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 591-50-4 iodobenzene 
• 447-53-0 1,2-Dihydronaphthalene 
• 201345-00-8 (E)-1-benzylidene-2-phenylcyclopropane 
• 14578-68-8 4-phenyl-3,4-dihydronaphthalen-1(2H)-one 

Downstream Products

• 132884-11-8 1-(o-benzylphenyl)allene 
• 132884-15-2 (Z)-1-(α-methoxybenzyl)-2-propen-1-ylbenzene 
• 85803-90-3 exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene 
• 132884-12-9 (1S,αS;1R,αR)-1-(α-methoxybenzyl)indan 
• 132884-16-3 1-(α-methoxybenzyl)-2-propen-2-ylbenzene 
• 132884-17-4 1-(1-methoxyprop-2-enyl)-2-benzylbenzene 
• 132884-12-9 (1R,αS;1S,αR)-1-(α-methoxybenzyl)indan 
• 132884-18-5 (Z)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene 
• 132884-13-0 (E)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene 
• 605-02-7 1-phenylnaphthalene 
• 3018-20-0 1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 13387-49-0 1-phenyl-1,4-dihydronaphthalene 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 
• 14090-18-7 cis-dibenzobicyclo<3.3.0>octa-2,7-diene 

Relevant academic research and scientific papers

Photocatalytic hydrogen-evolution dimerization of styrenes to synthesize 1,2-dihydro-1-arylnaphthalene derivatives using Acr+-Mes and cobaloxime catalysts

We report a hydrogen-evolution dimerization of styrenes via the synergistic merger of Acr+-Mes photocatalyst and cobaloxime proton reduction catalysts. By utilizing this dual catalyst system, 1,2-dihydro-1-arylnaphthalene derivatives can be directly constructed from commercially available styrenes. Our reaction proceeds smoothly under mild conditions without the need for oxidants or hydrogen atom transfer reagents, and the sole byproduct is hydrogen gas. Mechanistic investigation suggests that the reaction is initiated by photoinduced electron transfer under visible-light irradiation.

Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents

A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.

Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents

A protocol for palladium-catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one-pot method features a visible-light-mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium-catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn-1,4-selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.

Photoredox-Catalyzed Dimerization of Arylalkenes via an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives

We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9-mesityl-10-methylacridinium perchlorate) under visible light photocatalysis. In the presence of oxygen (in the air), the oxidative dimerization/intramolecular [4+2] cycloaddition of two alkene molecules provides 3,4-dihydronaphthalen-1(2H)-ones in good to high yields. Under a nitrogen atmosphere, (dihydro)naphthalenes were attained in moderate to excellent yields by using Selectfluor as the oxidant. The transformation proceeds via a tandem dimeric electrophilic addition/Friedel–Crafts cyclization/radical coupling/elimination sequence. This approach represents a mild and straightforward assembly of the naphthalene skeleton using a visible light photocatalytic cascade strategy. (Figure presented.).

New approach to 4-phenyl-β-aminotetralin from 4-(3-halophenyl)tetralen-2-ol phenylacetate

Mixed trifluoroacetyl phenylacetyl anhydride and 3-halostyrenes (fluoro, chloro, and bromo) or vinylcycloalkanes (cyclohexyl and cyclooctyl), undergo cascade Friedel-Crafts cycli-acylalkylation, enolization, and O-acylation to give 4-substituted tetralen-

Polycondensation of naphthalene and its alkyl derivatives

Polycondensation of naphthalene and its alkyl derivatives (stripping oil, 2,5-dimethylnaphthalene) in the presence of aluminum halides was performed. Under the action of an ultrasonic field on a benzene solution of naphthalene in the presence of the catalyst, intermolecular condensation and benzene addition are observed.

Divergent oxidative rearrangements in solution and in a zeolite: Distal vs proximal bond cleavage of methylenecyclopropanes

Irradiation of 9,10-dicyanoanthracene (DCA) or p-chloranil in the presence of E-1-benzylidene-2-phenylcyclopropane (E-5) in CH2CI2 causes E-5 to undergo methylenecyclopropane rearrangement. An adduct, Z-7, between DCA and 5 firmly supports the involvement of a bifunctional trimethylenemethane radical cation. In contrast, incorporation of E-5 into HZSM-5 produces trans,trans-1,4-diphenyl-1,3-butadiene radical cation sequestered in the HZSM-5 interior, tt-8·+ @ HZSM-5, identified by ESR and diffuse reflectance spectroscopy. In addition, low yields of tt-8, its cis, trans-isomer (ct-8), and 1-phenyl-1,2-dihydronaphthalene (9) were isolated from the supernatant solution. The sharp contrast between the photoinduced electrontransfer reaction with photosensitizers in solution and the spontaneous reaction with redox-active acidic zeolite offers the prospect of further zeolite-induced regiodivergent reactions in a range of additional substrates.

Competing Regiochemical Pathways in the Heck Arylation of 1,2-Dihydronaphthalene

The Heck reaction of aryl iodides with 1,2-dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1-aryl-1,2-dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3-aryl-1,2-dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd-H elimination pathway. The ratio always varies between 75:25 in favour of the 3-aryl product (Jeffery conditions) to 70:30 in favour of the 1-aryl product.

Thermolysis of Phenyl-substituted 1,2-Dihydronaphthalenes. Evidence for Diphenylbutadienes as Intermediates

The thermal rearrangement of the four phenyl-substituted 1,2-dihydronaphthalenes (15), (16), (19), and (20) have been studied by flash vacuum pyrolysis (FVP).By using the deuteriated starting compounds -(15) and -(16), it has been established that 1- and 4-phenyl-1,2-dihydronaphthalene (15) and (19) and 2- and 3-phenyl-1,2-dihydronaphthalene (16) and (20) are interconverted via the intermediates 1- and 2-phenyl-2,3-dihydronaphthalene (17) and (18), respectively, through two consecutive, sigmatropic 1,5-hydrogen shifts.In both processes partial oxidation to the corresponding phenylnaphthalenes (21) and (22) takes place.The deuterium distribution in the pyrolysis products suggests that in the hot zone diphenylbutadienes are formed, which are reconverted into phenyldihydronaphthalenes upon reaching the cold receiving flask.By FVP of 4-(p-tolyl)-1,2-dihydronaphthalene (34), 1-phenyl-1-(p-tolyl)butadiene (39), and 1-phenyl-4-(p-tolyl)butadiene (45) the latter type of interconversion could be confirmed.