1821-24-5

Usage

Uses

Used in Fragrance Industry:
1-(p-Tolyl)cyclohexanol is used as a fragrance ingredient for its distinctive floral, rose-like scent, contributing to the creation of perfumes and personal care products.
Used in Chemical Synthesis:
1-(p-Tolyl)cyclohexanol is utilized as an intermediate in the synthesis of other chemicals, playing a crucial role in the production of a range of compounds.
Used in Pharmaceutical Industry:
1-(p-Tolyl)cyclohexanol is employed as a pharmaceutical intermediate, indicating its potential use in the development and manufacturing of various medications.
Used in Solvent Applications:
This chemical is also used as a solvent, which is essential for dissolving, suspending, or extracting substances in numerous chemical processes and industries.
Used in Flavor and Fragrance Production:
1-(p-Tolyl)cyclohexanol is used in the production of flavors and fragrances, enhancing the sensory experience of various consumer products.

InChI:InChI=1/C13H18O/c1-11-5-7-12(8-6-11)13(14)9-3-2-4-10-13/h5-8,14H,2-4,9-10H2,1H3

Upstream product

• 108-94-1 cyclohexanone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 7732-18-5 water 
• 624-31-7 4-tolyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1821-23-4 1-cyclohex-1-enyl-4-methylbenzene 
• 644-08-6 4-Methylbiphenyl 
• 29479-97-8 1-(1-Chloro-cyclohexyl)-4-methyl-benzene 
• 52776-14-4 2-(4-methylphenyl)cyclohexanone 
• 21666-91-1 2-(p-tolyl)cyclohexan-1-ol 
• 52776-14-4 (R)-(-)-2-(4-methylphenyl)cyclohexanone 
• 167476-34-8 2-(4-methylphenyl)-1-(tert-butyldimethylsilyloxy)cyclohex-1-ene 
• 167476-38-2 (S)-(-)-2-(4-methylphenyl)cyclohexanone 
• 54750-40-2 1-(1,2-dimethylcyclopent-2-en-1-yl)-4-methylbenzene 
• 16982-00-6 1-(1,2,2-trimethylcyclopentyl)-4-methylbenzene 
• 100847-96-9 5-(p-toluoyl)valeric acid 
• 51941-57-2 (1R^*,2S^*)-1,2-Dimethyl-2-(4-methylphenyl)cyclopentanemethanol 
• 117421-36-0 6-oxo-6-(p-tolyl)hexanal 
• 117421-41-7 1-hydroxymethyl-5-methyl-5-p-tolylcyclopent-1-ene 

Relevant academic research and scientific papers

Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI

Grignard-type additions were readily achieved under the mediation of CuI (10 mol%) and samarium (2 equiv.) by employing various organohalides,e.g.benzyl, aryl, heterocyclic and aliphatic halides (Cl, Br or I), and diverse carbonyl compounds (e.g.carbonic esters, carboxylic esters, acid anhydrides, acyl chlorides, ketones, aldehydes, propylene epoxides and formamides) to afford alcohols, ketones and aldehydes, respectively, with high efficiency and chemoselectivity, in which the organosamarium intermediate might be involved.

Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents

We report the first terminal trifluoromethylation at aryl and alkyl ketones' ?, or more remote sites via the selective C-C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.

Halogen-Lithium Exchange of Sensitive (Hetero)aromatic Halides under Barbier Conditions in a Continuous Flow Set-Up

A halogen-lithium exchange reaction of (hetero)aromatic halides performed in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, and imines using BuLi as exchange reagent and a commercially available flow set-up is reported. The organolithiums generated in situ were instantaneously trapped with various electrophiles (Barbier conditions) resulting in the formation of polyfunctional (hetero)arenes. This method enables the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters, which are not tolerated in batch conditions.

Electrophotochemical Ring-Opening Bromination oftert-Cycloalkanols

An electrophotochemical ring-opening bromination of unstrainedtert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5- to 7-membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O-Br bond in hypobromite intermediates under visible light irradiation.

The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides

A novel, highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation of ketones and an unexpected cross-coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetrahydrofuran/toluene at 96°C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross-coupling have been attained under mild conditions. A novel reasonable mechanism involving a quinone intermediate is proposed. The high chemical selectivity in the cross-coupling to the hydroxy group of phenolic ketones should help ketones find new applications.

Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization

The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Bronsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.

Synthesis and antinociceptive behaviors of new methyl and hydroxyl derivatives of phencyclidine

Phencyclidine (I) and its derivatives show such pharmacological behaviors as analgesic, anticonsulvant, anti-anxiety and antidepressant, while interacting with central nervous system. In this study, new methyl and hydroxyl derivatives of PCP were synthesized and their antinociceptive behaviors in animals were examined by measuring the number of writhing in a writhing test of visceral pain and the pain scores in Formalin test. Compared to control and PCP groups, findings in experimental groups indicated the new synthesized analogues (compounds II, III and V, 10 mg/kg) of PCP were able to produce more analgesic effects in formalin and writhing tests, especially for compound V. It was concluded that the new synthesized derivatives of PCP could substantially and respectively diminish acute and chronic pains.

Synthesis and application of 2,6-bis(trifluoromethyl)-4-pyridyl phosphanes: The most electron-poor aryl phosphanes with moderate bulkiness

The poor will be rich: BFPy phosphanes (see scheme) mimic the electronic and steric characters of P(C6F5)3 and PPh 3, respectively. These novel ligands showed a large ligand acceleration effect on Stille coupling, the Rh-catalyzed 1,2-addition of aryl boronic acid to unactivated ketones and the asymmetric arylation of N-tosylimine using phenylboronic acid. Copyright

Broonsted acid-promoted hydrocyanation of arylalkenes

Nonactivated arylalkenes are effectively converted to tertiary benzylic nitriles in the presence of triflic acid and trimethylsilyl cyanide. The hydrocyanation reactions result in good to excellent yield when electron-donating groups are substituted on the benzene ring. The reaction conditions are mild and relatively safe, notably without need for handling hazardous hydrogen cyanide gas, providing simple and easy access to tertiary benzylic nitriles. The reaction was applied to the preparation of a PDE4 inhibitor (3) as well as a series of analogues.

Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Enantioselective protonation is a potent and efficient way to construct chiral carbons. Here we report details of the reaction using Lewis acid-assisted chiral Bronsted acids (chiral LBAs). The 1:1 coordinate complex of tin tetrachloride and optically active binaphthol ((R)- or (S)-BINOL) can directly protonate various silyl enol ethers and ketene disilyl acetals to give the corresponding α-aryl ketones and α-arylcarboxylic acids, respectively, with high enantiomeric excesses (up to 98% ee). A catalytic version of enantioselective protonation has also been achieved using stoichiometric amounts of 2,6-dimethylphenol and catalytic amounts of monomethyl ether of optically active BINOL in the presence of tin tetrachloride. This protonation is also effective for producing α-halocarbonyl compounds (up to 91% ee). DFT calculations on the B3LYP/LANL2DZ level show that the conformational structure of the chiral LBA and the orientation of activated proton on (R)-BINOLs are important for understanding the absolute stereochemistry of the products.