6921-43-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzene, 1-cyclopropyl-4-methyl-, serves as an intermediate in the production of pharmaceuticals. Its unique structure allows for the synthesis of various medicinal compounds, contributing to the development of new drugs and therapies.
Used in Pesticide Industry:
Benzene, 1-cyclopropyl-4-methylis also utilized as an intermediate in the manufacturing of pesticides. Its presence in the chemical structure of certain pesticides can enhance their effectiveness in controlling pests and protecting crops.
However, it is important to note that Benzene, 1-cyclopropyl-4-methyl-, has potential toxic and carcinogenic effects on human health. Therefore, proper safety measures and precautions should be taken when handling or working with Benzene, 1-cyclopropyl-4-methyl- to minimize any adverse effects.

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

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 75-11-6 diiodomethane 
• 67-66-3 chloroform 
• 873-49-4 cyclopropylbenzene 
• 74-88-4 methyl iodide 
• 1124-14-7 1-bromo-4-cyclopropylbenzene 
• 624-31-7 4-tolyl iodide 
• 23719-81-5 tri(cyclopropyl)indium 
• 106-38-7 para-bromotoluene 
• 411235-57-9 cyclopropylboronic acid 
• 4333-56-6 cyclopropyl bromide 
• 74-95-3 1,1-dibromomethane 
• 25628-09-5 tetramethylammonium trifluoromethanesulphonate 
• 85622-93-1 temozolomide 

Downstream Products

• 34835-98-8 1-phenyl-1-p-tolyl-propane 
• 104506-79-8 3-(4-Cyclopropyl-benzyl)-3-hydroxy-2-methyl-2,3-dihydro-benzo[f]isoindol-1-one 
• 104506-77-6 C₂₃H₂₁NO₂ 
• 3333-13-9 p-allyltoluene 
• 2077-29-4 (Z)-1-(4-tolyl)-1-propene 
• 2077-30-7 (E)-1-methyl-4-(prop-1-enyl)benzene 
• 1798-82-9 4-cyclopropylbenzoic acid 
• 56578-35-9 4-methyl-cinnamaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 90712-58-6 5-(p-tolyl)-4,5-dihydroisoxazole 
• 99273-70-8 5-(4-methylphenyl)-1,2-oxathiolane 2-oxide 
• 99273-70-8 5-(4-methylphenyl)-1,2-oxathiolane 2-oxide 
• 127506-37-0 (E)-3-(4-ethylphenyl)acrylaldehyde 
• 119200-33-8 5-(4-ethylphenyl)isoxazoline 

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.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

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.

Cyclopropanation of styrenes and stilbenes using lithiomethyl trimethylammonium triflate as methylene donor

Lithiomethyl trimethylammonium triflate, prepared from tetramethylammonium triflate, cyclopropanates several styrenes and stilbenes with electron-donating and selected electron-withdrawing substituents efficiently. Kinetic data support a stepwise nucleophilic addition-ring closure mechanism for this methylenation. This journal is the Partner Organisations 2014.

Diels-Alder reactions for the construction of cyclopropylarenes

The straightforward synthesis of new bicyclopropyl-substituted alkynes and 1,3-dienes and their application in cobalt-catalyzed Diels-Alder reactions are described. The cycloaddition processes generated the desired bicyclopropyl-substituted arene derivatives in moderate to good yields, depending on the steric congestion of the reaction partners. The regioselectivity of the cycloaddition was controlled by the ligand coordinated to the cobalt center. The cyclopropyl moiety remained unchanged over the course of the Diels-Alder reaction, indicating that no radical type intermediates were formed. Only in a single case did the DDQ oxidation of the primarily formed dihydroaromatic product lead to ring opening of a cyclopropyl subunit. In all of the other cases, cyclopropyl-modified arenes with various functionalities were obtained. Copyright

Lanthanum metal-assisted cyclopropanation of alkenes with gem-dihaloalkanes

It was confirmed that lanthanum metal was an efficient reagent for the reductive dehalogenation of gem-dihaloalkanes. When gem-dihaloalkanes were allowed to react with lanthanum metal in the presence of alkenes, cyclopropanation of the alkenes occurred under mild conditions giving the corresponding cyclopropanes in moderate to good yields.

Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.