620-85-9

Usage

Uses

Used in Fragrance Industry:
1-Benzyl-4-ethyl-benzene is used as a fragrance ingredient for its aromatic properties in various consumer products such as perfumes and cosmetics.
Used in Pharmaceutical Industry:
1-Benzyl-4-ethyl-benzene is used in the production of pharmaceuticals, contributing to the development of medicinal compounds.
Used as a Solvent in Industrial Processes:
1-Benzyl-4-ethyl-benzene serves as a solvent in various industrial processes, facilitating chemical reactions and material production.
Note: While 1-benzyl-4-ethyl-benzene has various applications, it may pose health risks, and proper safety measures should be taken when handling and using it.

InChI:InChI=1/C15H16/c1-2-13-8-10-15(11-9-13)12-14-6-4-3-5-7-14/h3-11H,2,12H2,1H3

Upstream product

• 18220-90-1 4-ethylbenzophenone 
• 10034-85-2 hydrogen iodide 
• 65189-90-4 4-(1-hydroxyethyl)benzophenone 
• 100-41-4 ethylbenzene 
• 100-51-6 benzyl alcohol 
• 3459-80-1 t-butoxymethylbenzene 
• 1137-42-4 4-Hydroxybenzophenone 
• 54852-64-1 ((octyloxy)methyl)benzene 
• 100-39-0 benzyl bromide 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 591-50-4 iodobenzene 
• 75251-24-0 1-(4-ethylphenyl)propan-2-one 
• 622-96-8 4-methylethylbenzene 
• 108-90-7 chlorobenzene 

Downstream Products

• 611-95-0 4-carboxybenzophenone 
• 66374-72-9 1-ethyl-4-cyclohexylmethyl-cyclohexane 
• 1530-03-6 1,1-diphenylpropane 
• 18220-90-1 4-ethylbenzophenone 
• 782-92-3 1-(4-benzylphenyl)ethanone 
• 53689-84-2 4-acetylbenzophenone 

Relevant academic research and scientific papers

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Scalable Continuous Synthesis of Organozinc Reagents and Their Immediate Subsequent Coupling Reactions

The continuous synthesis of organozinc reagents and their immediately following subsequent also continuous consumption in catalyzed and noncatalyzed coupling reactions were investigated. In the first step, a bed of Zn turnings at variable liquid throughputs and concentrations of organic halide solutions was used, and the formed Zn organometallics were analyzed for quality control. They were then directly pumped into a second step, namely, Reformatsky, Saytzeff, and Negishi coupling reactions. In the organozinc halides' formation, a novel process window was employed by using a large molar excess of Zn turnings and investigating mechanical as well as chemical Zn activation. Subsequent couplings of the freshly prepared Zn organometallics were done using examples of a Reformatsky, Saytzeff, and Negishi coupling reaction. For the Zn organometallics' formation, a laboratory-scale reactor setup previously built for Grignard reagent formation was evaluated including a Zn replenishing unit; the same reactor was also used in the metal-catalyzed subsequent step (Negishi coupling). The main objective of this work was to establish the scalable continuous formation of Zn organometallic reagents enabling fast and safe process optimization, analyze the reagents for their purity, and then immediately consume them in various follow-up steps, always only leaving a very small amount of reactive and sensitive organometallic reagent in the setup. It was found that full conversion of the employed halides could be achieved within a single passage through the reactor with organozinc yields of 82-92%, as well as being able to successfully perform subsequent non- and metal-catalyzed coupling steps with yields of up to 92%. A pilot-scale setup allowing a liquid throughput of up to 3-5 L/h has also been built and is ready to be tested with the synthesis as established here.

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions

Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides

A nickel-catalyzed cross-coupling of toluene derivatives with both aryl bromides and chlorides using a NIXANTPHOS-ligated nickel(II) complex has been developed. The key factor to success is proposed to be the catalyst activation of toluene by a cation-π complex, enabling methyl arenes (pKa ≈ 43) to be deprotonated with the relatively mild base NaN(SiMe3)2. This method facilitates access to a variety of sterically and electronically diverse hetero- and nonheteroaryl-containing diarylmethanes.

Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides

Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.

Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules

A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.

Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones

An original metal-free procedure for the synthesis of biarylmethanes is disclosed herein. The reactions occur with high selectivity starting from aryl iodides and benzylic ketones in the presence of superbasic media (CsOH/DMSO). This procedure allows a straightforward access to a wide range of biarylmethane derivatives substituted with electron-withdrawing and -donating substituents.

MoO3 supported on ordered mesoporous zirconium oxophosphate: An efficient and reusability solid acid catalyst for alkylation and esterification

A series of molybdenum oxide supported on ordered mesoporous zirconium oxophosphate (MoO3/M-ZrPO) materials with different MoO3 loadings (0–20 wt%) and calcination temperatures (500–900 °C) have been designed, synthesized and employed as solid acid catalysts in alkylation and esterification. The XRD, TG-DSC, H2-TPR, N2-physisorption and TEM characterizations were taken to investigate the structural properties and states of introduced MoO3 species. The influence of MoO3 loadings and calcination temperatures in catalytic performance was detailedly investigated and optimal catalytic activity was reached at 10 wt% MoO3 loadings and treated at 700 °C. Moreover, MoO3/M-ZrPO catalysts exhibited outstanding catalytic performance in Friedel-Crafts alkylation of different aromatic compounds and esterification of levulinic acid with 1-butanol. Furthermore, it was noteworthy that the catalyst had superior reusability and no noticeable declines were observed in catalytic performance even after seven runs.

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.

Continuous synthesis of organozinc halides coupled to Negishi reactions

The Negishi cross-coupling is a powerful C-C bond forming reaction. The method is less commonly used relative to other cross-coupling methods in part due to lack of availability of organozinc species. While organozinc species can be prepared, problems wit