873-49-4

Usage

Uses

Used in Chemical Synthesis:
Cyclopropylbenzene is used as a chemical intermediate in the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the formation of diverse chemical products through reactions like oxidation, reduction, and substitution.
Used in Research and Development:
Cyclopropylbenzene serves as a valuable compound in academic and industrial research for studying the properties and reactions of cyclopropylarenes. Its use in research helps to advance the understanding of the structure, reactivity, and potential applications of this class of compounds.
Used in Material Science:
Cyclopropylbenzene can be used as a building block for the development of new materials with specific properties, such as polymers with unique mechanical, thermal, or electrical characteristics. Its incorporation into polymer structures can lead to the creation of innovative materials for various applications.
Used in Pharmaceutical Industry:
Cyclopropylbenzene is used as a key component in the synthesis of certain pharmaceutical drugs. Its unique structure can contribute to the development of new drugs with improved efficacy, selectivity, and reduced side effects.
Used in Agrochemical Industry:
Cyclopropylbenzene can be utilized in the development of agrochemicals, such as pesticides and herbicides, with enhanced performance and reduced environmental impact. Its incorporation into agrochemical formulations can lead to the creation of more effective and sustainable products for agricultural use.

InChI:InChI=1/C9H10/c1-2-4-8(5-3-1)9-6-7-9/h1-5,9H,6-7H2

Upstream product

• 100-42-5 styrene 
• 75-11-6 diiodomethane 
• 14371-10-9 (E)-3-phenylpropenal 
• 2415-80-7 1,1-dichloro-2-phenylcyclopropane 
• 6120-95-2 1-phenyl-1-cyclopropane carboxylic acid 
• 124-41-4 sodium methylate 
• 17714-42-0 1,3-dibromo-1-phenylpropane 
• 90533-81-6 3-phenyl-pyrazolidine 
• 186581-53-3 diazomethane 
• 67-66-3 chloroform 
• 300-57-2 allylbenzene 
• 36456-49-2 2-Phenyl-1,3-dithiolane 1,1,3,3-tetraoxide 
• 110-82-7 cyclohexane 
• 84564-98-7 peracide phenyl-2-cyclopropane carboxyloque cis 

Downstream Products

• 73326-58-6 3-methoxy-3-phenyl-propylmercury ⁽¹⁺⁾; chloride 
• 124483-42-7 3-methoxy-3-phenyl-propylmercury ⁽¹⁺⁾; cyanide 
• 1530-03-6 1,1-diphenylpropane 
• 6921-44-4 4-nitrophenylcyclopropane 
• 10292-65-6 2-nitrophenylcyclopropane 
• 4489-23-0 1-bromo-4-(prop-1-en-1-yl)benzene 
• 2114-36-5 1-bromopropylbenzene 
• 17714-42-0 1,3-dibromo-1-phenylpropane 
• 27238-93-3 1-methoxy-4-(1-phenylpropyl)benzene 
• 6921-45-5 1-(4-cyclopropylphenyl)ethanone 
• 34835-98-8 1-phenyl-1-p-tolyl-propane 
• 13125-59-2 3-methoxy-1-phenylpropan-1-ol 
• 26278-67-1 1,3-dimethoxy-1-phenylpropane 
• 16510-81-9 3-methoxy-3-phenyl-propan-1-ol 

Relevant academic research and scientific papers

S-Alkylation of α-Thioether Iron Compounds by + and +

Treatment of the thiomethyl complexes (R=Me or Ph0 with + or (CO)2(=CH2)>+ results in S-alkylation, affording the sulphonium salts >+ and Fe(η-C5Me

Dichloromethane activation by chlorochromium(II) complexes with TpiPr2: Generation of an electrophilic Cr-methylene species without the action of an external Cl-abstraction reagent

Five-coordinated chlorochromium(II) complexes with TpiPr2 activate CH2Cl2 to give a metal-carbene species without the action of an external Cl-abstraction reagent, and the resulting methylene fragment is trapped by nucleop

Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions

We have developed a convenient development-scale reactor (0.44 mol/h) to prepare diazomethane from N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in ～80% yield. Diazomethane (CH2N2) made with this reactor is extracted into nitrogen gas from the liquid reaction mixture, effectively removing it from reagents and byproducts that may interfere in subsequent reactions. Vertically oriented tubular reactors were used to produce and consume diazomethane in situ. Key features of this reactor include high productivity and correspondingly low reactor volume (reactor volume/liquid flow rate = 6.5 min) and a commercially available gas/liquid separator equipped with a selectively permeating hydrophilic membrane. The design of the reactor keeps the inventory below 53 mg of CH2N2 during normal operation. The reactor was demonstrated by generating CH2N2 that was used in a connected continuous reactor. We evaluated esterification reactions and a continuous Pd-catalyzed cyclopropanation reaction with the reactor and achieved high conversion with 1.5 and 4.1 equiv of MNTS precursor, respectively.

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Air-Stable Iron-Based Precatalysts for Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters

The development of an air-stable iron(III)-based precatalyst for the Suzuki-Miyaura cross-coupling reaction of alkyl halides and unactivated aryl boronic esters is reported. Despite benefits to cost and toxicity, the proclivity of iron(II)-based complexes to undergo deactivationviaoxidation or hydrolysis is a limiting factor for their widespread use in cross-coupling reactions compared to palladium-based or nickel-based complexes. The new octahedral iron(III) complex demonstrates long-term stability on the benchtop as assessed by a combination of1H NMR spectroscopy, M?ssbauer spectroscopy, and its sustained catalytic activity after exposure to air. The improved stability of the iron-based catalyst facilitates an improved protocol in which Suzuki-Miyaura cross-coupling reactions of valuable substrates can be assembled without the use of a glovebox and access a diverse scope of products similar to reactions assembled in the glovebox with iron(II)-based catalysts.

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

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.

Formation of Cyclopropanes via Activation of (γ-Methoxy)alkyl Gold(I) Complexes with Lewis Acids

Treatment of the gold 3-methoxy-3-phenylpropyl complex (P)AuCH2CH2CH(OMe)Ph [P = P(t-Bu)2o-biphenyl] with AlCl3 at -78 °C led to the immediate (≤5 min) formation of a 4:1 mixture of phenylcyclopropane and (1-methoxypropyl)benzene in 86 ± 5% combined yield. Lewis acid activation of the stereochemically pure isotopomer erythro-(P)AuCH2CHDCH(OMe)Ph led to the formation of cis-2-deuterio-1-phenylcyclopropane in 84 ± 5% yield as a single stereoisomer, which established that cyclopropanation occurred with inversion of the γ-stereocenter. Similarly, ionization of the stereochemically pure cyclohexyl gold complex cis-(P)AuCHCH2CH(OMe)CH2CH2CH2 at -78 °C formed bicyclo[3.1.0]hexane in 82% ± 5% yield, which validated a low energy pathway for cyclopropanation involving inversion of the α-stereocenter. Taken together, these observations are consistent with a mechanism for cyclopropane formation involving backside displacement of both the Cγleaving group and the Cα (L)Au+ fragment via a W-shaped transition state.

The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation

The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.