606-97-3

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzyl-2-phenyl-benzene is utilized as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows it to be a versatile building block for creating a wide range of medicinal agents.
Used in Fragrance Industry:
As a fragrance ingredient, 1-benzyl-2-phenyl-benzene is employed for its aromatic properties, which are valuable in the formulation of perfumes and other cosmetic products. Its ability to impart distinctive scents makes it a sought-after component in the fragrance industry.
Used in Polymer Production:
In the polymer industry, 1-benzyl-2-phenyl-benzene is used in the production of polymers. Its chemical structure contributes to the development of polymers with specific properties, making it an important precursor in material science.
Used in Dye and Pigment Manufacturing:
1-Benzyl-2-phenyl-benzene also serves as a precursor in the manufacturing of dyes, pigments, and other industrial chemicals. Its aromatic nature allows it to be a fundamental component in the creation of a variety of colorants and specialty chemicals used across different industries.
Overall, 1-benzyl-2-phenyl-benzene's diverse applications in pharmaceuticals, fragrances, polymers, dyes, and pigments underscore its importance and value in the chemical industry.

Upstream product

• 92-52-4 biphenyl 
• 100-44-7 benzyl chloride 
• 118-92-3 anthranilic acid 
• 108-88-3 toluene 
• 16170-82-4 [14C]methyl iodide 
• 101-81-5 Diphenylmethane 
• 100-39-0 benzyl bromide 
• 123-72-8 butyraldehyde 
• 591-51-5 phenyllithium 
• 141819-13-8 n-butyl o-iodobenzyl telluride 
• 1985-32-6 2-phenylbenzophenone 
• 23265-32-9 1-(methylsulfonyl)-2-(phenyl)diazene 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 13326-10-8 benzyl methyl carbonate 

Downstream Products

• 789-62-8 2-Cyclohexylmethyl-bicyclohexyl 

Relevant academic research and scientific papers

Palladium-Catalyzed Cross-Coupling of Superbase-Generated C(sp3) Nucleophiles

A range of methods has been investigated recently for the arylation of weakly acidic C(sp3)-H bonds, primarily exploiting directed metalation with a transition metal catalyst or radical formation via hydrogen atom transfer. In this work, a classical base-mediated approach is taken, exploiting the ability of organometallic superbases to metalate very weakly acidic (pKa> 40) C-H bonds. Conditions are developed with eithern-BuLi/diamine orn-BuLi/KOtBu superbases to enable metalation to occur with high selectivity. Organolithium nucleophiles can be directly used in cross-coupling, or organozincs can be formed to enable reactions with functional group-dense organohalides.

Borane-catalyzed C(sp3)-F bond arylation and esterification enabled by transborylation

The activation and functionalization of carbon- fluorine bonds represent a significant synthetic challenge, given the high thermodynamic barrier to C-F bond cleavage. Stoichiometric hydridoborane-mediated C-F functionalization has recently emerged, but is yet to be rendered catalytic. Herein, the borane-catalyzed coupling of alkyl fluorides with arenes (carbon-carbon bond formation) and carboxylic acids (carbon-oxygen bond formation) has been developed using transborylation reactions to achieve catalytic turnover. Successful C-C and C-O coupling across a variety of structurally and electronically differentiated arenes and carboxylic acids was achieved using 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) as the catalyst and pinacolborane (HBpin), with broad functional group tolerance. Experimental and computational studies suggest a mechanistic dichotomy for the carbon-carbon and carbon-oxygen coupling reactions. B-F transborylation (B-F/B-H metathesis) between F-B-9-BBN and HBpin enabled catalytic turnover for carbon-carbon bond formation, whereas direct exchange between the alkyl fluoride and acyloxyboronic ester (C-F/B-O metathesis) was proposed for carbon-oxygen coupling, where H-B-9-BBN catalyzed the dehydrocoupling of the carboxylic acid with HBpin.

Interactions of C?F Bonds with Hydridoboranes: Reduction, Borylation and Friedel–Crafts Alkylation

The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN)

Immobilization of an Aminobisphosphine–PdII Complex over Graphene Oxide: An Efficient and Reusable Catalyst for Suzuki–Miyaura, Ullmann Coupling and Cyanation Reactions

The grafting of an aminobis(phosphine)–PdII complex (PNP–PdII) [PdCl2{(Ph2P)2N(CH2)3Si(OMe)3}] (2) on graphene oxide (GO) has been carried out by a condensation reaction between methoxysilane groups of 2 and hydroxyl groups of GO. The composite material was characterized by FTIR spectroscopy, solid-state 31P NMR spectroscopy, SEM, TEM, XPS and ICP-AES techniques. All these tools support the clean immobilization of compound 2 on GO. The composite material showed high catalytic activity in Suzuki–Miyaura, Ullmann coupling and cyanation reactions. The heterogeneity of the composite was confirmed by a hot filtration test. The immobilized PNP–PdII shows comparable activity to its homogeneous analogue 2. The recycling ability of the catalyst was examined for five consecutive runs, which showed little or no reduction in its catalytic efficiency.

A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

Use of Trifluoromethyl Groups for Catalytic Benzylation and Alkylation with Subsequent Hydrodefluorination

The electrophilic organofluorophosphonium catalyst [(C6F5)3PF][B(C6F5)4] is shown to effect benzylation or alkylation by aryl and alkyl CF3 groups with subsequent hydrodefluorination, thus resulting in a net transformation of CF3 into CH2-aryl fragments. In the case of alkyl CF3 groups, Friedel-Crafts alkylation by the difluorocarbocation proceeded without cation rearrangement, in contrast to the corresponding reactions of alkyl monofluorides.

Towards iron-catalysed suzuki biaryl cross-coupling: Unusual reactivity of 2-halobenzyl halides

The reaction of 2-halobenzyl halides with the borate anion Li[(Ph)(t-Bu)Bpin] leads not only to the expected arylation at the benzyl position, but also to some Suzuki biaryl cross-coupling. Preliminary mechanistic investigations hint towards the intermediacy of benzyl iron intermediates that can either: (a) directly cross-couple with the aryl boron reagent to give observed monoarylated species, or (b) undergo oxidative addition of the aryl halide to generate the diarylated species on reaction with the boron-based nucleophile.

Iron-catalyzed arylation of aromatic ketones and aldehydes mediated by organosilanes

A simple and efficient iron-catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4-% FeCl3 or Fe(acac) 3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel-Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel-Crafts alkylation reactions, robust applications for the synthesis of pharmaceutical intermediates and so on can be envisioned. A robust one-pot, iron-catalyzed chlorination Friedel-Crafts alkylation reaction of benzylic carbonyl compounds, mediated by chlorotrimethylsilane and triethylsilane, has been developed to yield substituted diaryl and triaryl building blocks. Copyright

Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: Experimental and computational studies

The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl 2(PCy3)2 to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.