796-30-5

Usage

Chemical classification

Polycyclic aromatic hydrocarbon (PAH)

Physical state

White crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Uses

Synthetic intermediate in the production of dyes, pharmaceuticals, and other organic compounds

Application

Research and development of new materials due to unique chemical and physical properties

Hazardous nature

Considered a hazardous substance

Safety precautions

Handle with care to avoid skin, eye, and respiratory system irritation

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 103-80-0 phenylacetyl chloride 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 4467-88-3 1,3-diphenylindene 
• 120413-69-6 1,4-diphenyl-1,4-dihydro-naphthalene-1,4-diol 
• 74563-25-0 1,3-Diphenyl-1,3-ethanophthalan 
• 77482-00-9 1,8-Diphenyl-9-phenylsulfanyl-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 77461-67-7 1,8-Diphenyl-9-phenylselanyl-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 77461-69-9 1,8-Diphenyl-9-(3-trifluoromethyl-phenylselanyl)-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 77971-09-6 1,4-Dihydro-9,9-dimethyl-1,4-diphenyl-1,4-silanonaphthalin 
• 104240-10-0 C₂₀H₁₄N₂^(2-)*2Na⁽¹⁺⁾ 
• 107-06-2 1,2-dichloro-ethane 
• 7641-46-5 (E,E)-1,4-dilithio-1,4-diphenyl-1,3-butadiene 
• 1614-12-6 1H-1,2,3-benzotriazol-1-amine 

Downstream Products

• 848-83-9 1,3-diphenylnaphthalene 
• 858431-24-0 1,4-diphenyl-[2]naphthylamine 
• 33753-12-7 2,3-diphenyl[1,4]naphthoquinone 
• 60011-39-4 5,8-diphenyl-1,4-naphthoquinone 
• 73585-55-4 4-hydroxy-2,4-diphenyl-1(4H)-naphthalenone 
• 408317-34-0 2-nitro-1,4-diphenyl-naphthalene 

Relevant academic research and scientific papers

Phenylnaphthalenes: Sublimation equilibrium, conjugation, and aromatic interactions

In this work, the interplay between structure and energetics in some representative phenylnaphthalenes is discussed from an experimental and theoretical perspective. For the compounds studied, the standard molar enthalpies, entropies and Gibbs energies of

Synthesis, C-H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

A series of 6-styryl-1,2-oxathiine 2,2-dioxides have been efficiently obtained by a two-step protocol from readily available (1E,4E)-1-(dimethylamino)-5-arylpenta-1,4-dien-3-ones involving a regioselective sulfene addition and subsequent Cope elimination. Pd-Mediated direct C-H bond functionalisation of the 6-styryl-1,2-oxathiine 2,2-dioxides and a wider selection of 5,6-diaryl substituted 1,2-oxathiine 2,2-dioxides proceeded smoothly to afford C-3 (hetero)aryl substituted analogues and the results are contrasted with those of a complementary bromination - Suzuki cross-coupling sequence. Whilst the cycloaddition of benzyne, derived fromin situfluoride initiated decomposition of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, to the substituted 1,2-oxathiine 2,2-dioxides resulted in low yields of substituted naphthalenes, the addition of 4-phenyl-1,2,4-triazoline-3,5-dione to the 6-styryl-1,2-oxathiine 2,2-dioxides afforded novel 5,9-dihydro-1H-[1,2]oxathiino[5,6-c][1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione 8,8-dioxides through a silica-mediated isomerisation of the initial [4 + 2] adducts.

Experimental and Computational Studies towards Chemoselective C?F over C?Cl Functionalisation: Reversible Oxidative Addition is the Key

Catalytic cross-coupling is a valuable tool for forming new carbon-carbon and carbon-heteroatom bonds, allowing access to a variety of structurally diverse compounds. However, for this methodology to reach its full potential, precise control over all competing cross-coupling sites in poly-functionalised building blocks is required. Carbon-fluorine bonds are one of the most stable bonds in organic chemistry, with oxidative addition at C?F being much more difficult than at other C-halide bonds. As such, the development of methods to chemoselectively functionalise the C?F position in poly-halogenated arenes would be very challenging if selectivity was to be induced at the oxidative addition step. However, metal-halide complexes exhibit different trends in reactivity to the parent haloarenes, with metal-fluoride complexes known to be very reactive towards transmetalation. In this current work we sought to exploit the divergent reactivity of Ni?Cl and Ni?F intermediates to develop a chemoselective C?F functionalisation protocol, where selectivity is controlled by the transmetalation step. Our experimental studies highlight that such an approach is feasible, with a number of nickel catalysts shown to facilitate Hiyama cross-coupling of 1-fluoronapthalene under base free conditions, while no cross-coupling with 1-chloronapthalene occurred. Computational and experimental studies revealed the importance of reversible C?Cl oxidative addition for the development of selective C?F functionalisation, with ligand effects on the potential for reversibility also presented.

Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions

Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.

Group 4 Diarylmetallocenes as Bespoke Aryne Precursors for Titanium-Catalyzed [2 + 2 + 2] Cycloaddition of Arynes and Alkynes

Despite the ubiquity of reports describing titanium (Ti)-catalyzed [2 + 2 + 2] cyclotrimerization of alkynes, the incorporation of arynes into this potent manifold has never been reported. The in situ generation of arynes often requires fluoride, which instead will react with the highly fluorophilic Ti center, suppressing productive catalysis. Herein, we describe the use of group 4 diarylmetallocenes, CpR2MAr2 (CpR = C5H5, C5Me5; M = Ti, Zr), as aryne precursors for the Ti-catalyzed synthesis of substituted naphthalenes via coupling with 2 equiv of an alkyne. Fair-to-good yields of the desired naphthalene products could be obtained with 1% catalyst loadings, which is roughly an order of magnitude lower than similar reactions catalyzed by palladium or nickel. Additionally, naphthalenes find broad applications in the electronics, photovoltaics, and pharmaceutical industries, urging the discovery of more economic syntheses. These results indicate that aryne transfer from a CpR2M(?2-aryne) complex to another metal is a viable route for the introduction of aryne fragments into organometallic catalytic processes.

Diels-alder reaction of isobenzofurans/cyclopentadienones with tetrathiafulvalene: Preparation of naphthalene, fluoranthene, and fluorenone derivatives

Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.

Ruthenium-Catalyzed Cycloisomerization of 2-Alkynylstyrenes via 1,2-Carbon Migration That Leads to Substituted Naphthalenes

A ruthenium-catalyzed carbocyclization of 2-alkynylstyrenes that involves a very rare 1,2-carbon migration of internal alkynes is reported. Various 1,2-di -and 1,4,7-trisubstituted naphthalenes are synthesized. Mechanistic studies revealed that this reaction proceeds via a disubstituted vinylidene complex as the key intermediate by 1,2-carbon migration of the 2-alkynylstyrenes.

NHC Hg(II) and Pd(II) complexes based on 1,8-dihydroxy-9,10-anthraquinone: synthesis, structure and catalysis

Three bis-azolium salts, 1,8-bis[3′-(N-R-azoliumyl)propoxy]-9,10-anthraquinone hexafluorophosphate L1H2(PF6)2-L2H2(PF6)2 (R = ethyl or picolyl, azoliumyl = imidazoliumyl or benzimidazoliumyl) and 1,3-bis[8′-(3′′-(N-ethyl-imidazoliumyl)propoxy)anthraquinon-l-yloxy]propane hexafluorophosphate (L3H2(PF6)2), as well as their three macrometallocycle N-heterocyclic carbene mercury(ii) complexes [L1′HgBr2] (1), [L2Hg](PF6)2 (3) and [L3Hg](PF6)2 (3) were prepared and characterized by 1H NMR and 13C NMR spectroscopy and X-ray crystallography. In complexes 1-3, each macrometallocycle (18-membered macrometallocycle for 1, one 18-membered and two 6-membered macrometallocycles for 2, and 28-membered macrometallocycle for 3) was formed by one biscarbene ligand (L1′ for 1, L2 for 2, and L3 for 3) and one Hg(ii) ion. Interestingly, the carbonyl group on the 9-position in complex 1 reacted with two acetonitrile molecules in the presence of the strong base KOtBu through losing one molecule of H2O to form L1′. As a result, two-CH2CN units were introduced to anthraquinone, in which the two-CH2CN units lie on two flanks of the anthraquinone plane. In the crystal packings of 1-3, 2D supramolecular layers and 3D supramolecular frameworks are formed via hydrogen bonds and ππ interactions. Additionally, the catalytic activity of the L1-Pd(ii) complex in situ in the Suzuki-Miyaura reaction was studied. The results show that this catalyst is efficient in the Suzuki-Miyaura reaction.

N-heterocyclic carbene palladium complex and preparation method and purpose thereof

The invention discloses a N-heterocyclic carbene palladium complex and a preparation method thereof, and the N-heterocyclic carbene palladium complex takes 1,8-dis[3-(N-ethyl imidazolyl)propanolato] anthraquinone hexafluorophosphate as a precursor, and the synthesized N-heterocyclic carbene palladium complex is used as a catalyst for catalyzing a carbon-carbon bond cross-coupling reaction. The preparation method comprises the following steps: under nitrogen protection, 1,8-dis[3-(N-ethyl imidazolyl)propanolato] anthraquinone hexafluorophosphate and a palladium compound are added in a reactionvessel according to a mol ratio being 2:1, an organic solvent is added, a reaction is carried out for 12-24 hours at the temperature of 0-100 DEG C, and filtering and ether diffusion are carried to obtain the N-heterocyclic carbene palladium complex. The prepared N-heterocyclic carbene palladium complex t is used for the technical field of the catalyst.

Catalytic activities of NHC-PdCl2 species based on functionalized tetradentate imidazolium salt in three types of C-C coupling reactions

A functionalized tetradentate imidazolium salt 9,10-bis{di[2′-(N-ethylimidazolium-1-yl)ethyl]aminomethyl}anthracene tetrakis(hexafluorophosphate) (1) has been synthesized and characterized. The catalytic activity of the NHC-PdCl2 species formed by compound 1 and PdCl2 was tested in Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions. The results showed that this catalytic system was effective for above three types of C-C coupling reactions.