5502-88-5

Usage

Uses

Used in Fragrance Production:
4-isopropyl-1-methylcyclohexene serves as a key component in the creation of fragrances, leveraging its sweet scent to enhance the aroma of various products. It is used for its aromatic properties to contribute to the overall olfactory experience of consumer goods.
Used as an Industrial Solvent:
In various industrial processes, 4-isopropyl-1-methylcyclohexene is utilized as a solvent. Its solvent properties make it suitable for dissolving and carrying other substances in different manufacturing applications, from the production of chemicals to the formulation of various products.
Used in Chemical Synthesis:
4-isopropyl-1-methylcyclohexene is also employed as an intermediate in chemical synthesis, where it can be transformed into other compounds that have specific uses in the chemical industry.
Used in Research and Development:
Due to its unique chemical structure, 4-isopropyl-1-methylcyclohexene is used in research settings to study chemical reactions and explore new methods of synthesis, potentially leading to the development of new materials and products.

Upstream product

• 499-69-4 (+/-)-menthol 
• 74233-53-7 1-p-menthanyl chloride 
• 3901-93-7 1-methyl-4-(1-methylethyl)cyclohexanol 
• 5989-27-5 D-limonene 
• 3626-19-5 1,2-epoxy-p-menthane 
• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 20536-36-1 neryl chloride 
• 1124-27-2 p-4⁽⁸⁾-menthene 
• 4952-03-8 1-methylcyclohexane hydroperoxide 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 500-00-5 3-p-menthene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 1879-07-8 cis-p-8-menthene 
• 80-15-9 Cumene hydroperoxide 

Downstream Products

• 101448-24-2 Diacetat des 1,2-Bis-hydroxymethyl-p-menthens-⁽⁵⁾ 
• 70985-57-8 4-Isopropyl-1-methyl-cyclohexanecarboxylic acid 
• 43205-82-9 carvotanacetone 
• 73011-52-6 4-Isopropyl-1-acetyl-cyclopenten-(1) 
• 103983-73-9 (5-Isopropyl-2-methylene-cyclohexyl)-methanol 
• 6007-05-2 (5-Isopropyl-2-methyl-cyclohex-1-enyl)-methanol 
• 82495-04-3 ((1R,5R)-5-Isopropyl-2,2-dimethyl-cyclohexyl)-methanol 
• 82495-04-3 ((1R,5S)-5-Isopropyl-2,2-dimethyl-cyclohexyl)-methanol 
• 110851-26-8 2-Iodo-4-isopropenyl-1-methyl-cyclohexane 
• 19860-79-8 6-Hydroxymethyl-p-menth-1-en 
• 74233-53-7 1-p-menthanyl chloride 
• 31383-92-3 6-bromo-p-menth-1-ene 
• 16741-95-0 p-menth-6-en-2-one semicarbazone 
• 2102-60-5 (+/-)-3,5-dinitro-benzoic acid-(trans-p-menth-6-en-2-yl ester) 

Relevant academic research and scientific papers

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Remarkable catalytic activity of polymeric membranes containing gel-trapped palladium nanoparticles for hydrogenation reactions

Polymeric flat-sheet membranes and hollow fibers were prepared via UV photo-initiated polymerization of acrylic acid at the surface of commercial polyether sulfones (PES) membranes. These polymeric materials permitted to immobilize efficiently palladium nanoparticles (PdNP), which exhibited a mean diameter in the range of 4?6 nm. These materials were synthesized by chemical reduction of Pd(II) precursors in the presence of the corresponding support. We successfully applied the as-prepared catalytic materials in hydrogenation reactions under continuous flow conditions. Flat sheet membranes were more active than hollow fibers due to the flow configuration and defavorable operating conditions. Actually, various functional groups (i.e. C[dbnd]C, C[tbnd]C and NO2) were reduced in flow-through configuration, under mild conditions (between 1.4 and 2.2 bar H2 at 60 °C, using 3.2 mol% of Pd loading), archiving high conversions in short reaction times (12?24 s).

Method for synthesizing bark beetle pheromone

The bark beetle pheromone is (1S, 4R) -4 - isopropyl -1 - methyl -2 -cyclohexene -1 - alcohol, and the synthetic method comprises the following steps: forming a clathrate compound with (S)- (-) - limonene and carrying out catalytic hydrogenation reaction

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

Photo-Initiated Cobalt-Catalyzed Radical Olefin Hydrogenation

Outer-sphere radical hydrogenation of olefins proceeds via stepwise hydrogen atom transfer (HAT) from transition metal hydride species to the substrate. Typical catalysts exhibit M?H bonds that are either too weak to efficiently activate H2 or too strong to reduce unactivated olefins. This contribution evaluates an alternative approach, that starts from a square-planar cobalt(II) hydride complex. Photoactivation results in Co?H bond homolysis. The three-coordinate cobalt(I) photoproduct binds H2 to give a dihydrogen complex, which is a strong hydrogen atom donor, enabling the stepwise hydrogenation of both styrenes and unactivated aliphatic olefins with H2 via HAT.

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.

Partial and Total Solvent-Free Limonene's Hydrogenation: Metals, Supports, Pressure, and Water Effects

Bio-based solvents menthene and menthane were obtained through limonene's partial and total hydrogenation under various catalytic conditions. Heterogeneous catalysts based on different active metals and supports (carbon, alumina, and silica) were systematically tested for solvent-free total and partial hydrogenation of limonene under high and low hydrogen pressure. Influences of these catalysts on the formation of menthene, menthane, and cymene, a dehydrogenated product, were determined. The impact of water addition on the conversion and selectivity of the catalysts was also investigated. Amongst all tested catalysts, Rh/Alumina which was never tested for total and partial hydrogenation of limonene was the most effective as 1-menthene was quantitatively produced at low pressure (0.275 MPa) while menthane was mostly obtained at a higher pressure (2.75 MPa). Water addition on Rh/Alumina favoured menthene production even at high pressure. To propose menthane, menthene, and menthane/menthene mixture as an alternative to fossil-based solvents such as n-hexane for the extraction of natural products, β-carotene, vanillin, and rosmarinic acid solubilizations have been investigated. If a modeling approach using COSMO-RS software predicted a comparable solubilization of these 3 compounds for the 3 solvents, experimental assays revealed that menthene solubilizes β-carotene, vanillin, and rosmarinic acid three to five times better than n-hexane.

Convenient synthesis of cobalt nanoparticles for the hydrogenation of quinolines in water

Easily accessible cobalt nanoparticles are prepared by hydrolysis of NaBH4 in the presence of inexpensive Co(ii) salts. The resulting material is an efficient catalyst for the hydrogenation of quinoline derivatives in water. The activity and chemoselectivity of this catalyst are comparable to other cobalt-based heterogeneous catalysts.

Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

With the aim of preparing bio-sourced supports with enhanced properties in catalysis, we devised an original strategy allowing the immobilization of metal nanoparticles. Thus, size-controlled hydrochars with a high degree of hydroxyl functionalities, from both neat sucrose or modified with acrylic acid (10 wt.%), were derivatized with ether linkers containing ammonium groups. These non-porous carbon-based materials were used as suitable supports for the immobilization of palladium nanoparticles. The catalytic materials were synthesized by reduction of Pd(OAc)2 to Pd(0) under H2 atmosphere in the presence of the corresponding hydrochar, and fully characterized by standard methods. Among the different hydrochar-supported palladium materials, those functionalized with tetraalkylammonium groups afforded heterogeneous catalysts, exhibiting high activity in hydrogenations of different types of substrates (alkynes, alkenes, and carbonyl and nitro derivatives). The most efficient catalyst was recycled up to ten runs without loss of catalytic behavior, in agreement with the unchanged composite materials after catalysis (Transmission Electron Microscopy (TEM) analyses) and the lack of metal leaching in the extracted organic products (no palladium detected by Inductively Coupled Plasma-Atomic Emission Spectrometry (ICP-AES)); these systems exhibited enhanced recyclability properties as compared to commercial Pd/C catalyst.