91766-85-7

Usage

Physical state

Colorless liquid

Molecular weight

188.7 g/mol

Uses

Intermediate in production of pharmaceuticals and agrochemicals, fragrance and flavoring agent in food and cosmetic industries, preparation of organic compounds, solvent in chemical reactions

Hazards

Harmful if swallowed, inhaled, or absorbed through the skin

Upstream product

• 4806-81-9 o-cyclohexylaniline 
• 542-18-7 cyclohexyl chloride 
• 108-90-7 chlorobenzene 
• 13248-54-9 cyclohexyl chloroformate 
• 110-82-7 cyclohexane 
• 66107-36-6 2-chlorophenyl triflate 
• 256390-55-3 cyclohexylzinc chloride 
• 95-57-8 2-monochlorophenol 
• 108-93-0 cyclohexanol 
• 108-94-1 cyclohexanone 
• 36692-27-0 2-chlorophenylmagnesium bromide 
• 7137-56-6 1-cyclohexyl-2-nitrobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 931-50-0 cyclohexylmagnesium bromide 

Downstream Products

• 118-91-2 ortho-chlorobenzoic acid 

Relevant academic research and scientific papers

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.

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.

Ruthenium-catalyzed para-selective oxidative cross-coupling of arenes and cycloalkanes

A novel, direct para-selective oxidative cross-coupling of benzene derivatives with cycloalkanes catalyzed by ruthenium was developed. A wide range of arenes bearing electron-withdrawing substituents was functionalized directly with simple cycloalkanes with high para-selectivity; arenes with electron-donating groups were mainly para-functionalized. Benzoic acid can be used directly.