14476-01-8

Basic information

• Product Name: Naphthalene, 1-(2-methylphenyl)-
• Synonyms: 1-o-tolyl-naphthalene;Naphthalene, 1-(2-methylphenyl)-
• CAS NO: 14476-01-8
• Molecular Formula: C17H14
• Molecular Weight: 218.298
• Mol File: 14476-01-8.mol
• Article Data: 85

Chemical Properties

• Melting Point: 63 °C
• Boiling Point: 334.6±17.0 °C(Predicted)
• Density: 1.064±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Naphthalene, 1-(2-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 1-(2-methylphenyl)-(14476-01-8)
• EPA Substance Registry System: Naphthalene, 1-(2-methylphenyl)-(14476-01-8)

Safety Data

• Hazardous Substances Data: 14476-01-8(Hazardous Substances Data)

Upstream product

• 90-11-9 1-Bromonaphthalene 
• 583-60-8 2-Methylcyclohexanone 
• 68971-87-9 (2-tolyl)tributyltin 
• 90-13-1 1-Chloronaphthalene 
• 932-31-0 ortho-tolylmagnesium bromide 
• 703-55-9 1-naphthylmagnesiumbromide 
• 16419-60-6 2-Methylphenylboronic acid 
• 91-20-3 naphthalene 
• 95-46-5 2-methylphenyl bromide 
• 7029-32-5 dinaphthalen-1-ylzinc 
• 13922-41-3 1-Naphthylboronic acid 
• 108-88-3 toluene 
• 1144-13-4 naphthalen-1-yl N,N-dimethylsulfamate 
• 96-09-3 styrene oxide 

Relevant articles and documents

New, potentially chelating NHC ligands; synthesis, complexation studies, and preliminary catalytic evaluation

Two new N-heterocyclic carbene (NHC) ligands bearing 2-morpholino and 2-piperidinyl naphthyl wingtips were synthesised (2-SIMorNap and 2-SIPipNap). Nuclear magnetic resonance studies, in conjunction with crystal structures and derivatisation of the NHC salts using a chiral counteranion, revealed that the ligand wingtips are oriented anti with respect to each other. From the free carbene, palladium, ruthenium and iridium complexes were prepared. NHC-iridium dicarbonyl complexes were made in order to extract the TEP values for these ligands. The study showed that these NHC ligands are more electron-donating than normal, aryl-substituted NHCs. The palladium complexes were tested in representative Suzuki-Miyaura cross-coupling reactions and compared to the state of the art systems. Ruthenium-catalysed ring-closing metathesis with these ligands was also performed. It was found that Grubbs’ 2nd generation catalyst incorporating 2-SIPipNap did not initiate at room temperature and required heating for RCM to occur.

Palladium-catalyzed arylative carbon - Carbon bond cleavage of α,α-disubstituted arylmethanols [11]

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Air-Stable [(R3P)PdCl2]2 Complexes of Neopentylphosphines as Cross-Coupling Precatalysts: Catalytic Application and Mechanism of Catalyst Activation and Deactivation

Air-stable [(R3P)PdCl2]2 complexes with di-tert-butylneopentylphosphine (DTBNpP, 1a) or trineopentylphosphine (TNpP, 1b) ligands have been applied to Suzuki cross-coupling reactions, and the mechanism of their conversion to the active LPd0 catalyst species has been studied. Precatalysts 1a,b provide effective catalysts for Suzuki cross-coupling of aryl bromides at room temperature, even when the reactions are performed in air. The precatalyst systems provided much higher activity catalysts in toluene/water in comparison to acetonitrile/water. Precatalyst loadings could be decreased by a factor of 50 in toluene in comparison to acetonitrile, while achieving equal or better yields. In acetonitrile/water, ligand metalation to form a [(κ2-P,C-DTBNpP)PdX]2 palladacycle was found to compete with formation of the active Pd(0) species. The palladacycle shows low catalytic activity; thus, its formation represents a catalyst deactivation pathway. In toluene, clean formation of the active Pd(0) species occurs without competitive palladacycle formation. The improved selectivity to form the active Pd(0) species in toluene appears to account for the higher activity of the precatalysts in toluene/water.

Carbon nanospheres with well-controlled nano-morphologies as support for palladium-catalyzed Suzuki coupling reaction

Uniform carbon nanospheres (UCS) with well-controlled nano-morphologies were fabricated by hydrothermal carbonization of sucrose in the presence of kayexalate. Highly dispersed and ultrafine palladium nanoparticles were supported on the UCS through a facile co-reduction process with NaBH4 as reducing agent. The obtained Pd@UCS exhibited efficient catalytic activity for the Suzuki coupling reaction. Moreover, the as-prepared catalyst could be recycled and reused at least five times without significant loss of its catalytic activity.

NHC-Pd(II)-Im (NHC = N-heterocyclic carbene; Im = 1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides

A new type of well-defined N-heterocyclic carbene (NHC)-palladium chloride-imidazole complexes derived from IPr HCl or IMes HCl, PdCl2 and 1-methylimidazole exhibits high catalytic activity in the room-temperature Suzuki-Miyaura coupling reactions of aryl or heteroaryl chlorides. Moreover, the large-scale (20.0 mmol) couplings in the presence of 0.01 mol% catalyst loading can also give the corresponding coupling products in high yields.

Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles

Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl - heteroaryl, aryl - alkenyl, and aryl - alkynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II) - chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.

Palladium-catalyzed Kumada reaction employing aminophosphine as ligand

In this article a palladium-catalyzed Kumada reaction was reported. The procedure was mild and tolerated a series of aryl bromides, affording the biaryls in good to excellent yield. Copyright Taylor & Francis Group, LLC.

Ferrocenyl phosphine-oxazaphospholidine oxide ligands for the Suzuki-Miyaura coupling of hindered aryl bromides and chlorides

A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki-Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.

C-H arylation of triphenylene, naphthalene and related arenes using Pd/C

A highly selective arylation of a number of polyaromatic hydrocarbons (PAHs) with aryliodonium salts and Pd/C as the only reagent is reported. The first C-H functionalization of triphenylene is explored, and proceeds at the most sterically hindered position. This non-chelate assisted C-H functionalization extends the reactivity profile of Pd/C and provides controlled access to π-extended PAHs, an important aspect of work towards the preparation of nanographenes. Mechanistic studies suggest in situ formation of catalytically active insoluble nanoparticles, and that the reaction likely proceeds via a Pd(0)/Pd(II) type reaction manifold.

A General Method for the Suzuki-Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature

The catalytic formation of di- and trisubstituted ortho biaryl junctions has been achieved using a palladacylce pre-catalyst bearing a N-heterocyclic carbene ligand. This transformation is performed at room temperature in technical grade 2-propanol. Copyr

Fe-Catalyzed Intramolecular Cross-Dehydrogenative Arylation (CDA), Efficient Synthesis of 1-Arylnaphthalenes and 4-Arylcoumarins

Direct cross-dehydrogenative coupling of different inert C?H bonds is the most straightforward and environmentally benign method to construct C?C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp3)H bond and aromatic C(sp2)H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization-dehydrogenation tandem process was proposed.

Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications

Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.