4501-35-3

Usage

Uses

Used in Chemical Production:
1-Cyclohexyl-2-methylbenzene is used as a precursor in the chemical industry for the production of phenol and acetone, which are essential for manufacturing various products, including resins, plastics, and pharmaceuticals.
Used as a Solvent:
Cumene serves as a solvent in various industrial applications, including the production of synthetic camphor and diphenyl oxide, due to its ability to dissolve a wide range of substances.
Used in the Production of Synthetic Camphor:
1-Cyclohexyl-2-methylbenzene is used as a starting material in the synthesis of synthetic camphor, which is an important ingredient in the fragrance and flavor industries.
Used in the Production of Diphenyl Oxide:
Cumene is also utilized in the production of diphenyl oxide, a chemical intermediate that is used in the synthesis of various organic compounds and pharmaceuticals.

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

Upstream product

• 22618-51-5 2'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 67-56-1 methanol 
• 626-62-0 Cyclohexyl iodide 
• 108-88-3 toluene 
• 75-05-8 acetonitrile 
• 110-83-8 cyclohexene 
• 108-93-0 cyclohexanol 
• 71-43-2 benzene 
• 108-94-1 cyclohexanone 
• 953-91-3 cyclohexyl tosylate 
• 7446-70-0 aluminium trichloride 
• 104-15-4 toluene-4-sulfonic acid 
• 60260-74-4 (methylsulfonyl)cyclohexane 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 87-83-2 pentabromotoluene 
• 97023-48-8 2-cyclohexylbenzoic acid 

Relevant academic research and scientific papers

Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents Using a Tetrachloroferrate with an Innocent Countercation

Bis(triphenylphosphoranylidene)ammonium tetrachloroferrate, (PPN)[FeCl4] (1), was evaluated as a catalyst for cross-coupling reactions. 1 exhibits high stability toward air and moisture and is an effective catalyst for the reaction of secondary alkyl halides with aryl Grignard reagents. The PPN cation is considered as an innocent counterpart to the iron center. We have developed an easy-to-handle iron catalyst for “ligand-free” cross-coupling reactions. (Figure presented.).

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.

Enantiospecific Synthesis of ortho-Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence

Coupling reactions between benzylamines and boronic esters have been investigated. ortho-Lithiated benzylamines react with boronic esters and a N-activator to afford ortho-substituted benzylic boronic esters with formal 1,1′-benzylidene insertion into the C-B bond. The reaction occurs by a SN2′ elimination and 1,2-metalate rearrangement of the N-activated boronate complex to afford a dearomatized intermediate, which undergoes a Lewis-acid catalyzed 1,3-borotropic shift to afford the boronic ester products in high yield and with excellent enantiospecificity. The use of enantioenriched α-substituted benzylamines gave the corresponding secondary boronic esters with high ee.

Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer

The construction of quaternary centers is a common challenge in the synthesis of complex materials and natural products. Current cross-coupling strategies that can be generalized for setting these centers are sparse and, when known, are typically predicated on the use of reactive organometallic reagents. To address this shortcoming a new, photoredox-Ni dual catalytic strategy for the cross-coupling of tertiary organoboron reagents with aryl halides is reported. In addition to details on the cross-coupling scope and limitations, full screening efforts and mechanistic experiments are communicated.

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.

Alkylations of Arylboronic Acids including Difluoroethylation/Trifluoroethylation via Nickel-Catalyzed Suzuki Cross-Coupling Reaction

An efficient alkylation method of functionalized alkyl halides under mild nickel-catalyzed C(sp3)-(sp2) Suzuki cross-coupling conditions is described. The features of this approach are excellent functional group compatibility, low cost nickel catalyst, and the use of a mild base. This is also the first successful example of the nickel-catalyzed direct 2,2-difluoroethylation or 2,2,2-trifluoroethylation of aryl-/heteroarylboronic acids.

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.

Efficient cross-coupling of aryl Grignard reagents with alkyl halides by recyclable ionic iron(iii) complexes bearing a bis(phenol)-functionalized benzimidazolium cation

A novel bis(phenol)-functionalized benzimidazolium salt, 1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium chloride (H 3LCl, 1), was designed and used to prepare ionic iron(iii) complexes of the type [H3L][FeX4] (X = Cl, 2; X = Br, 3). Both 2 and 3 were characterized by elemental analysis, Raman spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The catalytic performances of 2 and 3 in cross-coupling reactions using aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens were studied. This analysis shows that complex 2 has good potential for alkyl chloride-mediated coupling. In comparison, complex 3 showed slightly lower catalytic activity. After decanting the product contained in the ethereal layer, complex 2 could be recycled at least eight times without significant loss of catalytic activity.

IRON BISPHENOLATE COMPLEXES AND METHODS OF USE AND SYNTHESIS THEREOF

The present application, relates to iron bisphenolate complexes and methods of use and synthesis thereof. The iron complexes are prepared from tridentate or tetradentate ligands of Formula I: wherein R1 and R2 are as defined herein. Also provided are methods and processes of using the iron bisphenolate complexes as catalysts in cross-coupling reactions and in controlled radical polymerizations.