4575-46-6

Usage

Class

Alkylbenzenes (Organic compounds)

Physical State

Colorless liquid

Odor

Sweet, floral

Uses

a. Fragrance ingredient in perfumes and cosmetic products
b. Flavoring agent in the food industry
c. Precursor in the production of other chemicals

Stability

Relatively stable and non-reactive under normal conditions

Risks

a. Flammability
b. Harmful if inhaled or ingested in large quantities

Industrial and Commercial Applications

Primarily in the fragrance and flavor industries

InChI:InChI=1/C13H18/c1-11-6-5-9-13(10-11)12-7-3-2-4-8-12/h5-6,9-10,12H,2-4,7-8H2,1H3

Upstream product

• 22618-50-4 3'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 542-18-7 cyclohexyl chloride 
• 108-88-3 toluene 
• 108-93-0 cyclohexanol 
• 67-56-1 methanol 
• 626-62-0 Cyclohexyl iodide 
• 75-05-8 acetonitrile 
• 110-83-8 cyclohexene 
• 953-91-3 cyclohexyl tosylate 
• 108-94-1 cyclohexanone 
• 1596-09-4 2-Cyclohexyl-4-methyl-phenol 
• 4501-36-4 1-cyclohexyl-4-methylbenzene 
• 108-85-0 1-bromocyclohexane 
• 620-22-4 3-Methylbenzonitrile 

Downstream Products

• 107203-42-9 3-cyclohexyl-benzoic acid 
• 121-91-5 isophthalic acid 

Relevant academic research and scientific papers

Reductive activation of arenes: XV. Anionic products of m-tolynitrile reduction with sodium in liquid ammonia, and their alkylation

From results of oxidation, protonation, and alkylation of the products arising in one- or two-electron reduction of m-tolunitrile with sodium in liquid ammonia followed a conclusion that these products are respectively anion-radical of the compound and 3-methyl-1-cyano-2,5-cyclohexadienyl anion. The reaction of both reduction products with alkyl halides gives rise to compounds of ipso-alkylation with respect to cyano group: the corresponding alkyltoluenes and 1-alkyl-3-methyl-1-cyclohexadienes. The ratio of these products depends on the structure of alkyl halide. The possibility to prepare selectively m-alkyltoluenes by reaction of the product of two-electron reduction of m-tolunitrile with alkyl halides was demonstrated.

PREPARATION OF DIPHENYL COMPOUNDS

This disclosure relates to the preparation of diphenyl compounds, especially dimethylbiphenyl compounds, in which there is one methyl group on each ring, and their oxidized analogues. These compounds, and particularly alkylated biphenyl compounds and biphenylcarboxylic acids, alcohols and esters, are useful intermediates in the production of a variety of commercially valuable products, including polyesters and plasticizers for PVC and other polymer compositions.

Hydroconversion of Thiophene Derivatives over Dispersed Ni–Mo Sulfide Catalysts

Abstract: The activity of unsupported Ni–Mo sulfide catalysts is studied in the hydroconversion of benzothiophene and dibenzothiophenes in the temperature range of 340–380°С and at an increased H2 pressure and in the СО/H2О system. The structure of dispersed catalysts formed by the in situ high-temperature decomposition of oil-soluble precursors (molybdenum hexacarbonyl, nickel naphthenate) is investigated by TEM. Effects of СО/H2О molar ratio, water mass content in the system, and CO pressure on the activity of the catalysts and yields of the products are explored. It is shown that, in the СО/H2О system, the highest conversion of benzothiophene and dibenzothiophene is attained at a temperature of 380°С, a СО pressure of 5?MPa, and a СО/H2О molar ratio of 2. The introduction of alkyl substituents into a dibenzothiophene molecule causes a reduction in the rate of reaction that predominantly occurs via the hydrogenation of aromatic rings. The catalyst activities in hydrogenation under H2 pressure and in the СО/H2О system are comparable.

Liquid phase hydrodeoxygenation of anisole, 4-ethylphenol and benzofuran using Ni, Ru and Pd supported on USY zeolite

The objective of this work is to understand the role of metals on the hydrodeoxygenation (HDO) reaction pathways of three bio-oil model compounds. Ni, Ru and Pd were impregnated on USY zeolite, and the catalysts were characterized to determine metal reduction profile, surface concentration and nanoparticle size. Ru-USY and Pd-USY were completely reduced at a temperature below 450 °C, but Ni-USY still contained surface metal oxides after reduction. There was no indication of strong interactions between the metals and USY support. Anisole, 4-ethylphenol and benzofuran were used as bio-oil model compounds, in order to determine the effects of each metal on deoxygenation of methoxy-, phenol and furan functional groups, respectively. Pd-USY was the most effective HDO catalyst, exhibiting the highest turnover frequency for HDO of all three model compounds, in addition to and high selectivity to deoxygenated products. A mechanism was proposed for each model compound, and the kinetics of hydrogenation, dehydration, C–C coupling and ring-opening reactions were determined.

Sterically congested phosphonium borate acids as effective Br?nsted acid catalysts

Phosphonium borate acids [HPPh2(C6F5)][B(C6F5)4] (2), [HPMes2(C6F5)][B(C6F5)4] (3) and [HPMes(C6F5)2][B(C6F5)4] (4) were synthesized via heterolytic dihydrogen cleavage in the presence of triisopropylsilylium and characterized by spectroscopic and crystallographic methods. Br?nsted acid catalysis using compounds 2–4 proved to be efficient for a number of challenging reactions (namely ionic hydrogenation, hydroamination and hydroarylation), owing to the restrained nucleophilicity of the sterically hindered conjugate bases. Reactivity of compounds 2–4 suggests that their pKavalues are similar to that of diethyl oxonium acid.

Nickel-catalyzed selective oxidative radical cross-coupling: An effective strategy for inert Csp3-H functionalization

An effective strategy for inert Csp3-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp3-H arylation products in good yields.

Iron-catalyzed arene alkylation reactions with unactivated secondary alcohols

A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.

Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides

A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp3) - Br bonds in the presence of C(sp2) - Br bonds was achieved.

Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon

Esters, acids and acid chlorides can be converted via the intermediacy of their corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH·H2O and DDQ or in two steps with SOCl2/pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.

Alkylation on graphite in the absence of Lewis acids

Graphite is introduced as a convenient catalyst for alkylation of aromatic compounds and alcohols by benzyl, tertiary alkyl, and secondary alkyl halides in the absence of strong Lewis acids. Primary alkyl halides are not active under the reaction conditions.