643-58-3

Usage

Uses

Used in Chemical Synthesis:
2-Phenyltoluene is used as a chemical intermediate for the synthesis of various compounds, particularly in the production of fluorene. This is due to its ability to undergo cyclodehydrogenation and conversion to the fluorene nucleus when treated with a palladium catalyst.
Used in Research and Development:
2-Phenyltoluene serves as a valuable compound in the field of research and development, particularly in the study of radical anions and their behavior using density functional theory calculations. This helps in understanding the fundamental properties and potential applications of related organic compounds.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Phenyltoluene may have potential applications in the pharmaceutical industry as a starting material for the synthesis of various drugs or drug candidates, given its chemical properties and the ability to undergo specific chemical reactions.
Used in Material Science:
2-Phenyltoluene could be utilized in material science for the development of new materials or the modification of existing ones, taking advantage of its cyclodehydrogenation properties and its conversion to the fluorene nucleus, which may have unique properties and applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 3786, 1971 DOI: 10.1021/ja00744a048Organic Syntheses, Coll. Vol. 6, p. 747, 1988

Upstream product

• 6957-09-1 1-(2-methylphenyl)-1-cyclohexanol 
• 22618-51-5 2'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 100-34-5 benzene diazonium chloride 
• 2028-34-4 o-toluene-diazonium chloride 
• 56-23-5 tetrachloromethane 
• 118-75-2 chloranil 
• 6699-93-0 (2-methylphenyl)lithium 
• 108-90-7 chlorobenzene 
• 938-81-8 N-nitrosoacetanilide 
• 108-88-3 toluene 
• 2396-01-2 phenyl radical 
• 981-18-0 triphenyl(phenylazo)methane 
• 94-36-0 dibenzoyl peroxide 
• 95-53-4 o-toluidine 

Downstream Products

• 86-73-7 9H-fluorene 
• 38580-83-5 2-phenylbenzyl chloride 
• 19853-09-9 2-phenylbenzyl bromide 
• 50991-08-7 trans-2-Methyl-dicyclohexyl 
• 50991-08-7 cis-2-Methyl-dicyclohexyl 
• 92495-58-4 2-phenylbenzyl methyl ether 
• 127921-33-9 2-(Dimethoxymethyl)biphenyl 
• 132657-06-8 3,6,6-Trimethoxy-2-methyl-3-phenylcyclohexa-1,4-diene 
• 947-84-2 2-Biphenylcarboxylic acid 
• 1203-68-5 2-Phenylbenzaldehyde 
• 77776-12-6 2-Benzylsulfanylmethyl-biphenyl 
• 77776-09-1 1-(2-Biphenylyl)-3-phenyl-2-thiapropan-2,2-dioxid 
• 77776-11-5 1,6-Bis(2-biphenylyl)-2,5-dithiahexan-2,2,5,5-tetroxid 
• 486-25-9 9-fluorenone 

Relevant academic research and scientific papers

Instantaneous carbon-carbon bond formation using a microchannel reactor with a catalytic membrane

Instantaneous catalytic carbon-carbon bond forming reactions were achieved in a microchannel reactor having a polymeric palladium complex membrane. The catalytic membrane was constructed inside the microchannel via self-assembling complexation at the interface between the organic and aqueous phases flowing laminarly, where non-cross-linked polymer-bound phosphine and ammonium tetrachloropalladate dissolved, respectively. A palladium-catalyzed coupling reaction of aryl halides and arylboronic acids was performed using the microchannel reactor to give quantitative yields of biaryls within 4 s of retention time in the defined channel region. Copyright

Suzuki reactions in water catalyzed by an active and reusable PMO-type Pd(II) organometal catalyst with cage-like mesoporous structure

A novel Pd(II) organometal catalyst with three-dimensional (3D) cage-like Ia3d cubic mesoporous structure and high surface area was prepared. In comparison with the corresponding catalyst with two-dimensional (2D) P6mm hexagonal mesoporous structure, the as-prepared catalyst exhibited higher activities in the water-medium Suzuki coupling reactions owing to the diminished diffusion limit. It showed comparable efficiencies with the Pd(PPh 3)2Cl2 homogeneous catalyst and could be easily recycled and reused for five times without significant loss of activity.

Effective heterogeneous catalyst for suzuki-miyaura cross-coupling in aqueous media: Melamine cyanurate complex containing Pd species

A melamine cyanurate complex catalyst containing Pd(II) ions (denoted Pd/M-CA) was effective for Suzuki-Miyaura cross-coupling reactions in environmentally benign aqueous media at room temperature. The reaction conditions, such as the type of Pd species in Pd/M-CA, loading amounts of Pd, solvent, and substrate concentration, were investigated for optimization. In the presence of Pd/M-CA under the optimal conditions, cross-coupling reactions of a wide range of structurally diverse aryl halides and arylboronic acids containing functional groups proceeded smoothly to provide the corresponding products in high yields. In addition, the Pd/M-CA could be reused at least 5 times while maintaining high yields. The reduction of Pd(II) ions in Pd/M-CA to Pd(0) by NaBH4 enhanced the catalytic activity to provide a high turnover number (TON) of 17600 and turnover frequency (TOF) of 880 h-1.

Efficient visible-light-driven Suzuki coupling reaction over Co-doped BiOCl/Ce-doped Bi2O2CO3composites

Suzuki coupling reaction is a widely practiced protocol in organic synthesis for the formation of C-C bonds. The conventional process for this reaction usually involves high temperatures and noble metals. Hence, the development of a green, cost-effective photocatalytic system is an attractive and challenging strategy for the reaction. Here, we report a modified palladium-free Co-doped BiOCl/Ce-doped Bi2O2CO3(CBCB) composite, which shows high photocatalytic activity under white LED irradiation. At room temperature, an excellent yield (91%) of the desired cross-coupling product biphenyl was obtained in environmentally friendly solvents. Density functional calculations, together with the experimental results, show that the presence of Co and Ce ions results in the appearance of some impurity levels near the Fermi level of pure BiOCl and Bi2O2CO3, which decreases their forbidden bandwidth, thus ensuring higher light absorption and superior electronic conductivity. Moreover, the intimate interfacial contact between Co-doped BiOCl and Ce-doped Bi2O2CO3planes has a significant impact on the separation and transfer of photoinduced charge carriers, which ultimately leads to a remarkable increase in visible-light-driven photocatalytic activity.

Recyclable Pd(0)-Pd(II) composites formed from Pd(II) dimers with NHC ligands under Suzuki-Miyaura conditions

Dimeric complexes of the type [Pd(μ-X)X(NHC)]2 were employed in the Suzuki-Miyaura cross-coupling leading to 2-methylbiphenyl. The excellent activity of the studied dimers is perfectly illustrated by a TOF of up to 106 h-1. Mechanistic investigations with the application of TEM, XPS, and mercury poisoning tests provided an insight into the nature of the catalytic process. Accordingly, the reduction of the dimeric palladium complex [Pd(μ-X)X(NHC)]2 resulted in the formation of a composite containing Pd(0) nanoparticles protected by a layer of a Pd(II) species such as anions [PdBr4]2- or [PdBr3(NHC)]-. The in situ formation of Pd(0)-Pd(II) composites resulted in the high stability of the catalytic system, which was active in ten subsequent recycles without any additional protection.

An efficient parts-per-million α-Fe2O3 nanocluster/graphene oxide catalyst for Suzuki-Miyaura coupling reactions and 4-nitrophenol reduction in aqueous solution

A new α-Fe2O3 nanocluster/graphene oxide catalyst is found to be efficient in parts-per-million for Suzuki-Miyaura coupling and 4-nitrophenol reduction in aqueous solution, and this catalyst is recycled at least 4 times in good yields.

Orthometallated palladium trimers in C-C coupling reactions

A series of trimeric palladium complexes of the [Pd3(μ-Cl) 4(P-C)2] (P-C = orthometallated aryl phosphite) formula have been prepared and structurally characterized using 31P NMR and ESI-MS methods. The structure of [Pd3(μ2-Cl) 4{k2-P,C-P(O-o-CH3C6H 3)(O-o-CH3C6H4)2} 2], 1c, was determined by X-ray diffraction. It is compared with the structure of the dimeric complex [Pd2(μ-Cl)2{k 2-P,C-P(O-m-CH3C6H3)(O-m-CH 3C6H4)2}2], 3b. The trimeric palladium complexes very efficiently catalyzed the Suzuki-Miyaura and Hiyama reactions in ethane-1,2-diol and the Sonogashira cross-coupling in ionic liquids. The mercury test confirmed the homogeneous pathway of the Suzuki-Miyaura reaction, although Pd(0) nanoparticles were observed by TEM in the post-reaction mixture.

Palladium nanoparticle supported on metal-organic framework derived N-decorated nanoporous carbon as an efficient catalyst for the Suzuki coupling reaction

A novel catalyst made of Pd nanoparticles supported on the N-doped nanoporous carbon, which was derived from Al-based metal?organic frameworks, was successfully fabricated for the first time. The prepared catalyst was characterized by transmission electron microscopy, scanning electron microscope, X-ray diffraction, X-ray photoelectron spectroscopy and N2 adsorption. The as-obtained catalyst showed high catalytic activity for the Suzuki-Miyaura coupling reactions. The coupling reactions can be conducted at room temperature. The yields of the products were in the range from90% to 99%. The catalyst can be recycled and reused at least 6 consecutive cycles without any significant loss in catalytic activity.

A palladium Chugaev carbene complex as a modular, air-stable catalyst for Suzuki-Miyaura cross-coupling reactions

A new Chugaev-type palladium carbene complex was prepared via a convenient metal-templated route and fully characterized by X-ray crystallography, NMR, and IR. This complex proved effective as a precatalyst for Suzuki-Miyaura cross-coupling reactions of a range of aryl bromides, even under aerobic conditions, and its modular synthesis should allow for further catalyst fine-tuning.

Pd@UiO-66: An Efficient Catalyst for Suzuki-Miyaura Coupling Reaction at Mild Condition

In this paper, the palladium nanoparticles were successfully encapsulated in metal-organic framework material, UiO-66, by a facile approach. Based on the microwave-assisted method, the pores of UiO-66 were activated and the metal precursors were reduced at the same time in the presence of reducing agent. The obtained Pd@UiO-66 was characterized via transmission electron microscopy, powder X-ray diffraction, N2 adsorption and X-ray photoelectron spectroscopy. The Pd@UiO-66 exhibited efficient catalytic activity for the Suzuki-Miyaura coupling reactions at mild condition. Graphical Abstract: The palladium nanoparticles were successfully encapsulated in metal-organic framework material, UiO-66, by a facile approach. Based on the microwave-assisted method, the pores of UiO-66 were activated and the metal precursors were reduced at the same time in the presence of reducing agent. The obtained Pd@UiO-66 exhibited efficient catalytic activity for the Suzuki-Miyaura coupling reactions at mild condition.]