1798-84-1

Usage

Uses

Used in Chemical Synthesis:
Benzene, 1-chloro-4-cyclopropylis used as an intermediate in the synthesis of various organic compounds. Its unique structure, featuring a benzene ring with a chlorine atom and a cyclopropyl group, makes it a valuable building block for the creation of more complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzene, 1-chloro-4-cyclopropylis used as a starting material for the development of new drugs. Its chemical properties allow for further functionalization and modification, which can lead to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
Benzene, 1-chloro-4-cyclopropylis also utilized in the agrochemical industry, where it serves as a precursor for the synthesis of pesticides and other crop protection agents. Its reactivity and structural features enable the production of compounds with specific pesticidal properties.
Used in Material Science:
In the field of material science, Benzene, 1-chloro-4-cyclopropylis employed in the development of new materials with unique properties. Its incorporation into polymers and other materials can lead to the creation of substances with enhanced characteristics, such as improved stability or increased reactivity.
Overall, the applications of Benzene, 1-chloro-4-cyclopropylare diverse and span across various industries, highlighting its importance as a versatile chemical compound. However, due to its potential toxicity, strict safety measures must be adhered to during its synthesis, handling, and use.

InChI:InChI=1/C9H9Cl/c10-9-5-3-8(4-6-9)7-1-2-7/h3-7H,1-2H2

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 75-11-6 diiodomethane 
• 19714-76-2 1,3-Dibrom-1-(p-chlor-phenyl)-propan 
• 1798-83-0 1-(4-chlorophenyl)-3-dimethylamino-propan-1-one hydrochloride 
• 1607-29-0 bis((1-methylcyclopropyl)formyl)peroxide 
• 108-90-7 chlorobenzene 
• 873-49-4 cyclopropylbenzene 
• 74-95-3 1,1-dibromomethane 
• 106-39-8 bromochlorobenzene 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 75-09-2 dichloromethane 
• 411235-57-9 cyclopropylboronic acid 
• 106-48-9 4-chloro-phenol 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 

Downstream Products

• 125928-14-5 C₂₂H₁₈ClNO₂ 
• 125928-13-4 C₂₂H₁₈ClNO₂ 
• 2940-56-9 1-bromo-1-p-chlorophenylpropane 
• 64473-35-4 3-(4-chlorophenyl)propyl bromide 
• 152467-43-1 1-(4-chlorophenyl)-1,3-propanediol 
• 90712-54-2 5-(4-chlorophenyl)-4,5-dihydroisoxazole 
• 104902-30-9 5-chloro-2-cyclopropylaniline 

Relevant academic research and scientific papers

Indium-mediated, highly efficient cyclopropanation of olefins using CH 2I2 as methylene transfer reagent

The indium-mediated, one-pot cyclopropanation of a variety of olefins with methylene iodide proceeds smoothly with excellent yields of products.

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

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.).

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

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.

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.

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Dinuclear Ni complexes supported by naphthyridine-diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional-group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively low cyclopropane yields (≤20 %). These results constitute an entry into catalytic carbene transformations from oxidized methylene precursors.

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.