2415-80-7

Usage

Uses

Used in Chemical Synthesis:
(2,2-Dichlorocyclopropyl)benzene is used as an intermediate in the synthesis of various organic compounds, particularly p-(2,2-dichlorocyclopropyl)aniline. This application is due to its unique chemical structure, which allows for further functionalization and the creation of a wide range of products with different properties and uses.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2,2-Dichlorocyclopropyl)benzene may be utilized as a building block for the development of new drugs. Its specific chemical properties can be exploited to design molecules with targeted therapeutic effects, potentially leading to the creation of novel medications for various medical conditions.
Used in Agrochemical Industry:
(2,2-Dichlorocyclopropyl)benzene could also find applications in the agrochemical industry, where it may be used as a precursor for the development of new pesticides or other agricultural chemicals. Its unique structure and reactivity can be harnessed to create compounds with specific modes of action, contributing to the ongoing efforts to develop more effective and environmentally friendly agrochemicals.
Used in Dye and Pigment Industry:
The compound may also be employed in the dye and pigment industry, where it could be used to synthesize new dyes or pigments with improved properties. Its chemical structure may allow for the creation of colorants with enhanced stability, brightness, or other desirable characteristics, meeting the demands of various applications such as textiles, plastics, and printing inks.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 12, 1990Synthetic Communications, 25, p. 3821, 1995 DOI: 10.1080/00397919508011456Tetrahedron Letters, 16, p. 3013, 1975

InChI:InChI=1/C9H8Cl2/c10-9(11)6-8(9)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 67-66-3 chloroform 
• 56-23-5 tetrachloromethane 
• 75-09-2 dichloromethane 
• 75-25-2 Bromoform 
• 1126-71-2 N,N-dimethylphenethylamine 
• 74-95-3 1,1-dibromomethane 
• 96-09-3 styrene oxide 
• 123849-08-1 (-)-(R)-dichloromethyl p-tolyl sulfoxide 
• 866-23-9 diethyl (trichloromethyl)phosphonate 

Downstream Products

• 873-49-4 cyclopropylbenzene 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 18523-34-7 1,1-dimethoxy-2-phenylcyclopropane 
• 16510-80-8 methyl β-phenyl-β-methoxy-propionate 
• 18523-33-6 1,1-Bis-methylmercapto-2-phenyl-cyclopropan 
• 29667-51-4 1-chloro-2-phenylcyclopropane 
• 23970-89-0 2.5-Dichlor-3.4-diphenyl-1.5-hexadien 
• 23970-88-9 2.5-Dichlor-1.6-diphenyl-1.5-hexadien 
• 17651-00-2 (2-chlorocyclopropyl)benzene 
• 17650-99-6 (2-chlorocyclopropyl)benzene 
• 40641-93-8 1-(4-acetylphenyl)-2,2-dichlorocyclopropane 
• 54458-54-7 γ-1-Chlor-1-methyl-t-2-phenylcyclopropan 
• 54458-54-7 γ-1-Chlor-1-methyl-c-2-phenylcyclopropan 

Relevant academic research and scientific papers

Generation of 'naked' fluoride ions in unprecedentedly high concentrations from a fluoropalladium complex

An F-/Cl- ligand exchange in the stable organopalladium fluoro complex 1 generates naked fluoride ions in unusually high concentrations. The released Freadily fluorinates dichloromethane under exceedingly mild conditions and deprotonates chloroform to produce dichlorocarbene.

Phase-transfer catalytic dichlorocyclopropanation of styrene under the influence of ultrasound conditions - A kinetic study

The kinetics for dichlorocyclopropanation of styrene with an excess of chloroform were studied under phase-transfer catalysis and ultrasound irradiation conditions using aqueous sodium hydroxide as the base and benzyltriethylammonium bromide as a catalyst. The reaction was carried out at 35 °C under pseudo-first order conditions by keeping aqueous sodium hydroxide and chloroform in excess and was monitored by gas chromatography (GC). The effects of agitation speed, quaternary ammonium salts, amount of catalyst, amount of sodium hydroxide and temperature on the kinetics of the conversion were investigated.

Synthesis of gem-Dichlorocyclopropanes Using Liquid–Liquid Slug Flow

By analyzing the causes of precipitation and clogging in continuous flow dichlorocyclopropanation, we established that the flow reaction can be performed only with T-junctions and microtubes. Unlike tertiary amines, when quaternary ammonium salts were used as PTCs, precipitation and clogging in microchannels did not occur, and an excellent yield of up to 99% was obtained after optimizing the reaction temperature, reactant concentration, and retention time. In the scale-up experiment, the reaction yields slightly decreased as the inner diameter (ID) of the microchannel was increased, but the calculated throughput increased from 2.41 g/h (ID: 1.5 mm) to 3.46 g/h (ID: 1.9 mm) and 5.13 g/h (ID: 2.4 mm).

DIHALOMETHANES AS C-H ACIDS IN THE CATALYTIC TWO-PHASE (CTP) SYSTEM - A NEW METHOD FOR THE SYNTHESIS OF gem-DICHLOROCYCLOPROPANES

Dihalomethanes react with carbon tetrachloride and alkenes in the CTP system affording gem-dichlorocyclopropanes.

Isotope effects and the mechanism of deoxygenation of epoxides with dichlorocarbene

The deoxygenation of styrene oxide with dichlorocarbene is studied by a combination of isotope effects and theoretical calculations. A normal 13C isotope effect of 1.016 is observed for the α-carbon of the styrene oxide but a surprising inverse isotope effect of 0.995 is observed at the β-carbon. This is indicative of a highly asynchronous process in which the Cα-O bond is broken without any progress in the breakage of Cβ-O bond. Theoretical calculations support this interpretation. This coarctate reaction is formally concerted as it avoids involving a high-energy intermediate, but it appears uninfluenced by transition state aromaticity.

Synthesis and Catalytic Activity of Quaternary Ammonium Salts Containing gem-Dichlorocyclopropane and 1,3-Dioxolane Fragments

Abstract: Quaternary ammonium salts containing gem-dichlorocyclopropane and 1,3-dioxolane groups were synthesized in high yield. The reactions of dichlorocarbonation of styrene and O-alkylation of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane in the presence of quaternary ammonium salts were studied. It was established that in the O-alkylation reaction, compounds containing cycloacetal and allyl moieties have the maximum efficiency in the series of catalysts studied. The structures of the isolated salts were proved by 1H and 13C NMR spectroscopy.

Grafted Polyethylene Glycol–Graphene Oxide as a Novel Triphase Catalyst for Carbenes and Nucleophilic Substitution Reactions

Abstract: Separation and reusability had been main problems for the using of polyethylene glycol (PEG) as phase transfer catalysts (PTCs). To solve these problems, PEG was firstly and successfully grafted on graphene oxide (GO) using BF3·C2H5OC2H5 as Lewis acid catalyst. The solid GO-PEG composites were systemically investigated by characterization techniques (TG, FT-IR, XPS, ICP-AES etc.) and then applied to some carbenes and nucleophilic substitution reactions as novel triphase catalysts. As the results, GO-PEG showed not only equally excellent catalytic activity (≥ 93% yield of 7,7-dichlorobicyclo[4.1.0]heptane and iodooctane) but also incomparable reusability (≥ 85% yield of iodooctane after using for four times) in comparison with traditional PTCs (PEG). Graphic Abstract: [Figure not available: see fulltext.].

Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an α-aryl group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey’s oxazaborolidine catalyst. Specifically, the TIPS nitronate with an α-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer

A rotor-stator homogenizer was found to be an effective mixing tool that accelerated solid-liquid phase-transfer reactions. In the asymmetric alkylation under phase-transfer conditions using the homogenizer, a considerably high turnover frequency was observed. (Figure presented.).

Phase-transfer and other types of catalysis with cyclopropenium ions

Abstract This work establishes the cyclopropenium ion as a viable platform for efficient phase-transfer catalysis of a diverse range of organic transformations. The amenability of these catalysts to large-scale synthesis and structural modification is demonstrated. Evaluation of the molecular structure of an optimal catalyst reveals some unique structural features of these systems. Finally, a discussion of electronic charge distribution underscores an important consideration for catalyst design. Aromatic ions: Tris(dialkylamino)cyclopropenium ions are shown to be effective carbocationic phase-transfer catalysts for a variety of mainstay transformations. The cyclopropenium platform is shown to be modular and accessible on scale. An X-ray structure and electron-density map revealed some unique features of this architecture (see scheme).