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Usage

Uses

Used in Flavor and Fragrance Industry:
4-Cyclohexyl-benzoic acid methyl ester is used as a flavoring or fragrance ingredient in various products, such as perfumes and cosmetics. Its unique scent profile makes it a valuable addition to these formulations, enhancing the sensory experience for consumers.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-cyclohexyl-benzoic acid methyl ester may have potential applications in the pharmaceutical industry. Given its chemical structure, it could potentially be utilized in the development of new drugs or as an intermediate in the synthesis of pharmaceutical compounds.
Used in Agricultural Industry:
Similarly, the potential applications of 4-cyclohexyl-benzoic acid methyl ester in the agricultural industry are not detailed in the materials. However, it could be explored for use in the development of agrochemicals, such as pesticides or herbicides, due to its chemical properties.
Safety Precautions:
As with any chemical, it is important to exercise caution when handling and using 4-cyclohexyl-benzoic acid methyl ester. Proper safety precautions should be followed to minimize potential risks, ensuring the well-being of both individuals and the environment.

InChI:InChI=1/C14H18O2/c1-16-14(15)13-9-7-12(8-10-13)11-5-3-2-4-6-11/h7-11H,2-6H2,1H3

Upstream product

• 67-56-1 methanol 
• 20029-52-1 4-cyclohexylbenzoic acid 
• 186581-53-3 diazomethane 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 108-85-0 1-bromocyclohexane 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 372-46-3 fluorocyclohexane 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 695-12-5 vinylcyclohexane 
• 110-82-7 cyclohexane 
• 626-62-0 Cyclohexyl iodide 
• 720-75-2 methyl 4-phenylbenzoate 
• 110-83-8 cyclohexene 

Downstream Products

• 252552-35-5 1-(4-cyclohexylphenyl)-2,2,2-trifluoroethan-1-one 
• 1456602-25-7 diethyl 4-(N-(4-cyclohexylbenzyl)-4-phenoxybenzamido)benzylphosphonate 
• 1456602-26-8 diethyl 3-(N-(4-cyclohexylbenzyl)-4-phenoxybenzamido)benzylphosphonate 
• 1456602-24-6 diethyl 3-(N-(4-cyclohexylbenzyl)-4-phenoxybenzamido)phenylphosphonate 
• 1456602-23-5 diethyl 4-(N-(4-cyclohexylbenzyl)-4-phenoxybenzamido)phenylphosphonate 
• 111818-33-8 1-(bromomethyl)-4-cyclohexylbenzene 
• 1367608-58-9 4-cyclohexylbenzyl(triphenyl)phosphonium bromide 

Relevant academic research and scientific papers

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.

Rapid and Direct Photocatalytic C(sp3)?H Acylation and Arylation in Flow

Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)?C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.

Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in waterviasynergistic nickel and copper catalysis

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developedvianickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale.

Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)-C(sp3) and C(sp3)-C(sp3) Bond Formation

The construction of C-C bonds through cross-coupling between two electrophiles in the absence of excess metallic reducing agents is a desirable objective in chemistry. Here, we show that N-alkylpyridinium salts can be efficiently merged with aryl or alkyl halides in an intermolecular fashion, affording products in up to 92% yield at ambient temperature. These reactions harness the ability of N-alkylpyridinium salts to form electron donor-acceptor complexes with Hantzsch esters, enabling photoinduced single-electron transfer and fragmentation to afford alkyl radicals that are subsequently trapped by a Ni-based catalytic species to promote C(sp2)-C(sp3) and C(sp3)-C(sp3) bond formation. The operationally simple protocol is applicable to site-selective cross-coupling and tolerates diverse functional groups, including those that are sensitive toward metal reductants.

Mild and Selective Rhodium-Catalyzed Transfer Hydrogenation of Functionalized Arenes

Diboron-mediated rhodium-catalyzed transfer hydrogenation of functionalized arenes is reported. In addition to good functional group tolerance, the reaction features operational simplicity and controllable chemoselectivity. The general applicability of this procedure is demonstrated by the selective hydrogenation of a range of arenes, including functionalized benzenes, biphenyls, and polyaromatics.

Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets

Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chemistry in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging.

Redox-Neutral Nickel(II) Catalysis: Hydroarylation of Unactivated Alkenes with Arylboronic Acids

Reported here is the discovery of a redox-neutral NiII/NiII catalytic cycle which is capable of the linear-selective hydroarylation of unactivated alkenes with arylboronic acids for the first time. This novel catalytic cycle, enabled

Ni-catalyzed Reductive Deaminative Arylation at sp3 Carbon Centers

A Ni-catalyzed reductive deaminative arylation at unactivated sp3 carbon centers is described. This operationally simple and user-friendly protocol exhibits excellent chemoselectivity profile and broad substrate scope, thus complementing existing metal-catalyzed cross-coupling reactions to forge sp3 C-C linkages. These virtues have been assessed in the context of late-stage functionalization, hence providing a strategic advantage to reliably generate structure diversity with amine-containing drugs.

Direct arylation of strong aliphatic C–H bonds

Despite the widespread success of transition-metal-catalysed cross-coupling methodologies, considerable limitations still exist in reactions at sp3-hybridized carbon atoms, with most approaches relying on prefunctionalized alkylmetal or bromide coupling partners1,2. Although the use of native functional groups (for example, carboxylic acids, alkenes and alcohols) has improved the overall efficiency of such transformations by expanding the range of potential feedstocks3–5, the direct functionalization of carbon–hydrogen (C–H) bonds—the most abundant moiety in organic molecules—represents a more ideal approach to molecular construction. In recent years, an impressive range of reactions that form C(sp3)–heteroatom bonds from strong C–H bonds has been reported6,7. Additionally, valuable technologies have been developed for the formation of carbon–carbon bonds from the corresponding C(sp3)–H bonds via substrate-directed transition-metal C–H insertion8, undirected C–H insertion by captodative rhodium carbenoid complexes9, or hydrogen atom transfer from weak, hydridic C–H bonds by electrophilic open-shell species10–14. Despite these advances, a mild and general platform for the coupling of strong, neutral C(sp3)–H bonds with aryl electrophiles has not been realized. Here we describe a protocol for the direct C(sp3) arylation of a diverse set of aliphatic, C–H bond-containing organic frameworks through the combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and nickel catalysis. This dual-catalytic manifold enables the generation of carbon-centred radicals from strong, neutral C–H bonds, which thereafter act as nucleophiles in nickel-mediated cross-coupling with aryl bromides to afford C(sp3)–C(sp2) cross-coupled products. This technology enables unprecedented, single-step access to a broad array of complex, medicinally relevant molecules directly from natural products and chemical feedstocks through functionalization at sites that are unreactive under traditional methods.