4030-17-5

Usage

Uses

Used in Flavor and Fragrance Industry:
4-cyclopropylanisole is used as a flavor and fragrance ingredient for its sweet and fruity aroma, enhancing the sensory experience of various consumer products.
Used in Pharmaceutical Industry:
4-cyclopropylanisole is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 4-cyclopropylanisole serves as a building block for the synthesis of other organic compounds, expanding the range of chemical products and applications.

InChI:InChI=1/C10H12O/c1-11-10-6-4-9(5-7-10)8-2-3-8/h4-8H,2-3H2,1H3

Upstream product

• 32293-33-7 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole 
• 38365-53-6 p-(2,2-dichlorocyclopropyl)anisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 106-96-7 propargyl bromide 
• 925-90-6 ethylmagnesium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 2973-86-6 lithium thiophenoxide 
• 23719-80-4 cyclopropylmagnesium bromide 
• 874-90-8 4-methoxybenzonitrile 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 637-69-4 4-Methoxystyrene 
• 74-88-4 methyl iodide 
• 696-62-8 para-iodoanisole 
• 1217362-94-1 di-tert-butoxy(cyclopropyl)silanol 

Downstream Products

• 27238-93-3 1-methoxy-4-(1-phenylpropyl)benzene 
• 59117-58-7 3-(4-methoxyphenyl)propyl methyl ether 
• 66832-94-8 4-cyclopropylphenyl ethyl ether 
• 40791-03-5 4-Methoxy-3-nitrophenylcyclopropane 
• 76469-32-4 2-nitro-4-cyclopropylphenyl ethyl ether 
• 591-50-4 iodobenzene 
• 94848-52-9 (3-iodo-4-methoxyphenyl)cyclopropane 
• 74387-14-7 1-cyclopropyl-4-methoxy-2-nitrobenzene 
• 90712-59-7 5-(4-methoxyphenyl)-4,5-dihydroisoxazole 
• 81484-46-0 2-bromo-4-cyclopropyl-1-methoxybenzene 
• 79415-36-4 1,3-bis(trifluoroacetoxy)-1-(p-methoxyphenyl)propane 
• 50741-91-8 2-nitro-4-cyclopropylphenol 
• 77197-94-5 2,6-dinitro-4-cyclopropylphenol 
• 70760-15-5 1-(4'-Methoxyphenyl)-1,3-propanediol 

Relevant academic research and scientific papers

Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions

Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.

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.

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.

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.

A Stereoconvergent Cyclopropanation Reaction of Styrenes

The first stereoconvergent cyclopropanation reaction by means of photoredox catalysis using diiodomethane as the methylene source is described. This transformation exhibits broad functional group tolerance and it is characterized by an excellent stereocontrol en route to trans-cyclopropanes regardless of whether E- or Z-styrene substrates were utilized.

Light-Mediated Reductive Debromination of Unactivated Alkyl and Aryl Bromides

Cleavage of carbon-halogen bonds via either single-electron reduction or atom transfer is a powerful transformation in the construction of complex molecules. In particular, mild, selective hydrodehalogenations provide an excellent follow-up to the application of halogen atoms as directing groups or the utilization of atom transfer radical addition (ATRA) chemistry for the production of hydrocarbons. Here we combine the mechanistic properties of photoredox catalysis and silane-mediated atom transfer chemistry to accomplish the hydrodebromination of carbon-bromide bonds. The resulting method is performed under visible light irradiation in an open vessel and is capable of the efficient reduction of a variety of unactivated alkyl and aryl substrates.

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.

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.

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,