1077-16-3

Usage

Uses

Used in Industrial Processes:
1-Phenylhexane is used as a solvent for its ability to dissolve a variety of substances, facilitating numerous chemical reactions and processes in the industry.
Used in Pharmaceutical Applications:
1-Phenylhexane is utilized as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medicines.
Used in Organic Synthesis:
As a key component in organic synthesis, 1-Phenylhexane is employed as a reactant or building block for the creation of more complex organic molecules, which can be used in a range of chemical products and materials.

InChI:InChI=1/C12H18/c1-2-3-4-6-9-12-10-7-5-8-11-12/h5,7-8,10-11H,2-4,6,9H2,1H3

Upstream product

• 106-98-9 1-butylene 
• 100-41-4 ethylbenzene 
• 110-53-2 1-Bromopentane 
• 1121-53-5 benzyl sodium 
• 4410-78-0 (cyclopentylmethyl)benzene 
• 942-92-7 caprophenone 
• 29898-25-7 1-phenylhexan-3-one 
• 4431-89-4 (cyclopentylmethyl)cyclohexane 
• 543-59-9 1-Chloropentane 
• 100-44-7 benzyl chloride 
• 1822-71-5 n-pentylsodium 
• 109-72-8 n-butyllithium 
• 4455-09-8 2-phenylethyl tosylate 
• 100-42-5 styrene 

Downstream Products

• 41297-13-6 (E)-4-(4-hexylphenyl)-4-oxobut-2-enoic acid 
• 21643-38-9 4-hexylbenzoic acid 
• 4292-75-5 n-hexylcyclohexane 
• 87-82-1 hexabromobenzene 
• 33228-45-4 4-hexylaniline 
• 1141-93-1 4-hexyl-benzenesulfonic acid amide 
• 25590-01-6 4-hexyl-benzenesulfonic acid 
• 5558-47-4 2-Phenylheptanoic acid 
• 37878-40-3 N,N'-(4-hexyl-m-phenylene)-bis-acetamide 
• 64357-41-1 (4-n-hexylphenyl)(phenyl)methanone 
• 79219-16-2 1-(4-hexyl-phenyl)-propan-1-one 
• 37592-72-6 1-(4-hexyl-phenyl)-ethanone 
• 58999-67-0 1-chloromethyl-4-hexylbenzene 
• 49763-69-1 4-hexylbenzaldehyde 

Relevant academic research and scientific papers

Copper-catalyzed semihydrogenation of alkynes to Z -alkenes

Copper-catalyzed semihydrogenation of internal alkynes has been developed. The reaction proceeds under an atmosphere of hydrogen (5 atm) at 100 °C in the presence of a readily available [(PPh3)CuCl]4 catalyst to give various Z-alkenes stereoselectively.

Isolated Organometallic Nickel(III) and Nickel(IV) Complexes Relevant to Carbon-Carbon Bond Formation Reactions

Nickel-catalyzed cross-coupling reactions are experiencing a dramatic resurgence in recent years given their ability to employ a wider range of electrophiles as well as promote stereospecific or stereoselective transformations. In contrast to the extensively studied Pd catalysts that generally employ diamagnetic intermediates, Ni systems can more easily access various oxidation states including odd-electron configurations. For example, organometallic NiIII intermediates with aryl and/or alkyl ligands are commonly proposed as the active intermediates in cross-coupling reactions. Herein, we report the first isolated NiIII-dialkyl complex and show that this species is involved in stoichiometric and catalytic C-C bond formation reactions. Interestingly, the rate of C-C bond formation from a NiIII center is enhanced in the presence of an oxidant, suggesting the involvement of transient NiIV species. Indeed, such a NiIV species was observed and characterized spectroscopically for a nickelacycle system. Overall, these studies suggest that both NiIII and NiIV species could play an important role in a range of Ni-catalyzed cross-coupling reactions, especially those involving alkyl substrates.

Electrolytically Induced Allene-Alkyne Isomerization

Preparative-scale electrolyses at mercury cathodes in dimethylformamide containing tetra-n-butylammonium perchlorate have revealed that 1-phenyl-1,2-hexadiene exhibits no evidence of isomerization to form 1-phenyl-1-hexyne via an electrolytically induced, base-catalyzed rearrangement; similarly, 1-phenyl-1,2-butadiene exhibits only a slight tendency (1-2percent) to form 1-phenyl-1-butyne.In contrast, voltammetric and electrolytic experiments demonstrate that isomerization of 1-phenyl-1-butyne, 1-phenyl-1-pentyne, and 1-phenyl-1-hexyne to the corresponding allenes occurs muchmore readily.Observations from several investigations show that the extent of allene-to-alkyne rearrangement increases from 1-phenyl-1,2-hexadiene to 1-phenyl-1,2-butadiene to phenylpropadiene, whereas the reverse alkyne-to-allene isomerization decreases in significance from 1-phenyl-1-hexyne to 1-phenyl-1-pentyne to 1-phenyl-1-butyne to 1-phenyl-1-propyne.Steric and electronic factors, which affect protonation of the conjugate bases of the various starting materials at acrbons 1 and 3, can be invoked to explain these trends.

Efficient synthesis of amylbenzenes over zeolite catalysts

The liquid-phase heterogeneous alkylation of benzene with 2-methyl-2-butene takes place actively and selectively over large-pore zeolite catalysts, which implies an environmentally friendly route for the synthesis of fert-amylbenzene. Copyright

Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters

Primary alcohols can be deoxygenated cleanly and in yields of 60-95% by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it simple and convenient.

Relevance of Single-Transmetalated Resting States in Iron-Mediated Cross-Couplings: Unexpected Role of σ-Donating Additives

Control of the transmetalation degree of organoiron(II) species is a critical parameter in numerous Fe-catalyzed cross-couplings to ensure the success of the process. In this report, we however demonstrate that the selective formation of a monotransmetalated FeII species during the catalytic regime counterintuitively does not alone ensure an efficient suppression of the nucleophile homocoupling side reaction. It is conversely shown that a fine control of the transmetalation degree of the transient FeIII intermediates obtained after the activation of alkyl electrophiles by a single-electron transfer (SET), achievable using σ-donating additives, accounts for the selectivity of the cross-coupling pathway. This report shows for the first time that both coordination spheres of FeII resting states and FeIII short-lived intermediates must be efficiently tuned during the catalytic regime to ensure high coupling selectivities.

N-Hexane activation over zeolites: Aromatic alkylation to 1-phenylhexane

Terminal 1-phenylhexane was observed during alkylation of benzene with n-hexane over 10-membered ring zeolites at moderate temperature, whereas it was not observed when 1-hexene was the reactant. The Royal Society of Chemistry 2010.

Nanocage catalysts - Rhodium nanoclusters encapsulated with dendrimers as accessible and stable catalysts for olefin and nitroarene hydrogenations

The phenylazomethine dendrimer generation 4 (TPP-DPA G4) and polyamidoamine dendrimer (PAMAM G4-OH) encapsulating rhodium nanocluster were found to be highly effective for olefin and nitroarene hydrogenations, affording high TOF (up to 17520 h-1); the important feature of the nanocage catalyst is that substrates can pass through the branches of the protecting groups of nanoclusters without releasing nanoclusters from the dendrimer. The Royal Society of Chemistry.

Arylation of hydrocarbons enabled by organosilicon reagents and weakly coordinating anions

Over the past 80 years, phenyl cation intermediates have been implicated in a variety of C-H arylation reactions. Although these examples have inspired several theoretical and mechanistic studies, aryl cation equivalents have received limited attention in organic methodology. Their high-energy, promiscuous reactivity profiles have hampered applications in selective intermolecular processes. We report a reaction design that overcomes these challenges. Specifically, we found that b-silicon-stabilized aryl cation equivalents, generated via silylium-mediated fluoride activation, undergo insertion into sp3 and sp2 C-H bonds. This reaction manifold provides a framework for the catalytic arylation of hydrocarbons, including simple alkanes such as methane. This process uses low loadings of Earth-abundant initiators (1 to 5 mole percent) and occurs under mild conditions (30° to 100°C).

Reactivity of mixed organozinc and mixed organocopper reagents. Part 4: A kinetic study of group transfer selectivity in C-C coupling of mixed diorganocuprates

The competitive rate data and Taft relationships for the coupling of bromomagnesium n-butyl (substituted phenyl) cuprates with alkyl bromides show that selective n-butyl transfer can be explained by an oxidative addition mechanism. Taft reaction constants