16510-27-3

Usage

Uses

Used in Flavor and Fragrance Industry:
1-Cyclopropylmethyl-4-methoxybenzene is used as a flavoring agent for its distinctive anise-like, sweet-spicy note. It adds a unique and pleasant aroma to various food products and beverages.
Used in Perfumery:
1-Cyclopropylmethyl-4-methoxybenzene is utilized as a fixative in perfumery, helping to stabilize and prolong the scent of fragrances. Its sweet-spicy aroma contributes to the overall complexity and depth of perfume compositions.
Used in Pharmaceutical Industry:
1-Cyclopropylmethyl-4-methoxybenzene is employed as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
1-Cyclopropylmethyl-4-methoxybenzene serves as a key intermediate in the production of agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for the development of effective and environmentally friendly agricultural products.

Trade name

Toscanol (Givaudan).

InChI:InChI=1/C11H14O/c1-12-11-6-4-10(5-7-11)8-9-2-3-9/h4-7,9H,2-3,8H2,1H3

Upstream product

• 140-67-0 Estragole 
• 54879-64-0 N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 56079-40-4 N,N-ditosyl-4-methoxybenzylamine 
• 23719-80-4 cyclopropylmagnesium bromide 
• 2393-23-9 4-methoxy-benzylamine 
• 6552-45-0 α-cyclopropyl(4-methoxyphenyl)methanol 
• 63559-26-2 2-(p-methoxybenzyl)propane-1,3-diol 
• 4333-56-6 cyclopropyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 52178-88-8 2-(4-methoxybenzyl)-1,1-dichlorocyclopropane 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 70106-27-3 2-(4-methoxyphenyl)cyclobutan-1-one 
• 100-17-4 para-methoxynitrobenzene 
• 119-27-7 2,4-dinitroanisole 
• 1412494-27-9 5-(4-methoxybenzyl)-4,5-dihydroisoxazole 
• 207120-89-6 (E)-4-(4-methoxyphenyl)but-3-enal 
• 854001-12-0 (Z)-5-(4-methoxyphenyl)pent-4-enoic acid: 
• 5724-06-1 (4E)-5-(4-methoxyphenyl)pent-4-enoic acid 

Relevant academic research and scientific papers

Photoredox/Nickel Dual Catalysis Enables the Synthesis of Alkyl Cyclopropanes via C(sp3)-C(sp3) Cross Electrophile Coupling of Unactivated Alkyl Electrophiles

A facile synthesis of mono-, 1,1- and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis is demonstrated. The challenging intramolecular C(sp3)-C(sp3) cross-electrophile coupling of readily available unactivated 1,3-dialkyl electrophiles was performed under mild conditions that allowed traditionally reactive functional groups to be included. Mechanistic inspection and control experiments revealed the importance of dual catalysis and that the reaction proceeds via a stepwise oxidative addition followed by an intramolecular SN2 reaction.

Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides

The aromatic ring in benzyl halides and sulfonates imparts unique reactivity at the benzylic carbon atom. Photoredox sp3-sp3 cross-coupling proved ineffective for coupling p-methoxybenzyl chloride (PMBCl), leading to a new strategy for the sp3-sp3 cross-coupling of benzyl halides and sulfonates. This strategy involved LiCl-accelerated synthesis of a Grignard reagent followed by a copper-catalyzed cross-coupling. The conditions worked well for PMBCl due to its exceptional reactivity but other benzyl bromides or sulfonates reacted poorly.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

A process of converting a carbon-carbon multiple bond to a cyclopropane ring, comprising the addition of a N-alkyl-N-nitroso compound to a mixture of alkene precursor, aqueous base and Pd(II)-catalyst, with the N-alkyl-N-nitroso compound obtained directly from an alkyl amine derivative, NaNO2 and an acid via phase separation of the N-alkyl-N-nitroso compound from the aqueous phase.

Iron-catalyzed π-activated C-O ether bond cleavage with C-C and C-H bond formation

A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C sp 3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3-sp3 C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent. A mild, economical, and environmentally friendly method for the construction of C sp 3-C sp 3 bonds through iron-catalyzed π-activated C-O ether bond cleavage is developed. In addition, this catalytic system can be used for the selective reduction of benzylic and allylic C-O ether bonds to C-H bonds. Copyright

Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation

A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C sp 3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3-sp3 C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent.

Cross-coupling of grignard reagents with sulfonyl-activated sp3 carbon-nitrogen bonds

Sulfonyl-activated sp3 carbon-nitrogen bonds have been found to be cleaved by Grignard reagents in the presence of 5 mol% of copper(I) iodide (CuI). Significantly, a broad range of sulfonyl-activated benzylic, allylic, and propargylic amines smoothly undergo the cross-coupling reaction with Grignard reagents to afford structurally diverse coupling products in good to excellent yields and with high chemo-, regio-, and stereoselectivity. Moreover, an S N2 mechanism has been demonstrated to be involved in the cross-coupling reaction that allows the asymmetric synthesis of chiral hydrocarbons from optically active α-branched amine derivatives. Copyright

Cyclopropyl- and allyl-substituted arenes in reaction with dinitrogen tetroxide. Effect of substrate oxidation potential on reaction direction

A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH2Cl2 and CH3CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The

Fragrance and flavour compositions

The invention relates to phenyl-cycloalkanes of formula (I) wherein the groups R1 to R6 are defined in the specification.

Vinyl Cations. 41. Influence of 4-Aryl and 4-Alkyl Substituents on the ?-Route Solvolyses of Homopropargyl Esters

The four 4-substituted-homopropargyl tosylates and triflates 6b-e (R=phenyl, p-tolyl, anisyl, and cyclopropyl) have been synthesized and solvolyzed under various conditions, as have 2-cyclopropyl-1-cyclobutenyl triflate (11-OTf) and nonaflate (11-ONf).In addition, the solvolyses of pent-3-yn-1-yl tosylate (6a-OTs, R=methyl) and triflate (prepared previously) are reported.The ratios of C-3 ring to C-4 ring 3 ring/C4ring)> products are recorded for the reactions in various solvents.As expected, ring closure (kΔ) increases and solvent displacement (kS, SN2) decreases with decreasing nucleophilicity of solvent.Temperature effects are noted for the sovolyses of tosylates 6a-e in 100percent TFE buffered with Na2CO3 in which kΔ increases with increasing temperature.The result is explained by decomposition of the intimate ion pair with temperature, whereupon elimination to the enyne becomes smaller and ring closure (kΔ) increases at the expense of elimination.The possibility of intervention of nonclassical vinyl cations is discussed, as are other mechanistic implications.