27546-46-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Benzene, 1-cyclopropyl-2-methylis utilized as a key building block in the synthesis of a variety of pharmaceuticals and agrochemicals. Its unique structure allows for the creation of complex molecules that can have specific therapeutic or pesticidal properties.
Used as a Solvent:
In various chemical processes, Benzene, 1-cyclopropyl-2-methylserves as a solvent, facilitating reactions and aiding in the dissolution of other substances that may be insoluble in water.
Used in Dye, Flavor, and Fragrance Production:
Benzene, 1-cyclopropyl-2-methylis employed as a chemical intermediate in the production of dyes, flavors, and fragrances, contributing to the development of a wide range of colorants, taste enhancers, and aromatic compounds.

InChI:InChI=1/C10H12/c1-8-4-2-3-5-10(8)9-6-7-9/h2-5,9H,6-7H2,1H3

Upstream product

• 75-11-6 diiodomethane 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 873-49-4 cyclopropylbenzene 
• 74-88-4 methyl iodide 
• 67-66-3 chloroform 
• 1607-29-0 bis((1-methylcyclopropyl)formyl)peroxide 
• 108-88-3 toluene 
• 95-46-5 2-methylphenyl bromide 
• 411235-57-9 cyclopropylboronic acid 
• 20034-51-9 2-cyclopropylbenzaldehyde 
• 23719-80-4 cyclopropylmagnesium bromide 

Downstream Products

• 71096-19-0 7-(4-Cyclopropyl-3-methyl-phenyl)-cyclohepta-1,3,5-triene 
• 1587-04-8 1-methyl-2-(2-propenyl)-benzene 
• 7399-49-7 1-methyl-2-(prop-1-en-2-yl)benzene 
• 2077-33-0 1-methyl-2-[(1Z)-prop-1-en-1-yl]benzene 
• 2077-34-1 (E)-1-(o-methylphenyl)-1-propene 
• 71096-12-3 4-Brom-1-cyclopropyl-2-methylbenzol 

Relevant academic research and scientific papers

The copper-catalyzed ring-opening reactions of cyclopropanes by N-fluorobenzenesulfonimide toward N-allylsulfonamides

In this paper, we reported a copper-catalyzed ring-opening reaction of arylcyclopropanes by N-fluorobenzenesulfonimide, leading to N-allylsulfonamides in moderate to good yields. This procedure tolerated bromo, fluoro, trifluoromethyl, phenyl and alkyl groups in the phenyl, proceeding with a sequential ring-opening of arylcyclopropanes, and copper-mediated β-H elimination of alkyl radical.

Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes

A silylium-ion-promoted ring-opening hydrosilylation of unactivated cyclopropanes is reported. The reaction is facilitated by the γ-silicon effect, and the regioselectivity is influenced by various stabilizing effects on the carbenium-ion intermediates, including the β-silicon effect. The experimental observations are in accord with the computed reaction mechanism. The work also showcases the ability of silylium ions to isomerize cyclopropyl to allyl groups, and the resulting α-olefins engage in a silylium-ion-mediated disilylation with hexamethyldisilane.

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.

Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate

We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochemical, two purely chemical-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a "unifying" chain propagation mechanism beyond initiation, tied by a common intermediate. In all, the proposed mechanism herein is substantiated by product distribution studies, kinetic analyses, LFERs, Rehm-Weller estimations of ΔGET, competition experiments, KIEs, fluorescence data, and DFT calculations. From a more physical standpoint, transient-absorption experiments have allowed direct spectroscopic observation of radical ion intermediates (previously only postulated or probed indirectly in photochemical fluorination systems) and, consequently, have provided kinetic support for chain propagation. Lastly, calculations suggest that solvent may play an important role in the cyclopropane ring-opening step.

Regioselective Metalation of Phenylcyclopropane and Smooth Addition of 1-Phenylcyclopropyl Potassium onto Ethylene

Whereas pentyl sodium in pentane mainly promotes a hydrogen/metal exchange reaction at the m- and p-position of phenylcyclopropane, both the butyllithium/potassium t-butoxide reagent and trimethylsilylmethyl potassium in tetrahydrofuran convert phenylcyclopropane exclusively into 1-phenylcyclopropyl potassium.The latter organometallic derivative adds smoothly onto the double bond of ethylene at temperatures around -40 deg.