40122-37-0

Usage

Physical form

White crystalline solid

Odor

Faint

Common uses

Synthetic intermediate in pharmaceuticals and agrochemicals

Chemical structure

Cyclopropane derivative with a tolyl group (benzene ring with a methyl group attached)

Properties

Insecticidal and fungicidal

Applications

Pesticides, fine chemicals, organic synthesis reactions

Safety precautions

May be harmful if ingested, inhaled, or in contact with skin

Upstream product

• 534-07-6 1,3-Dichloroacetone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 925-90-6 ethylmagnesium bromide 
• 186581-53-3 diazomethane 
• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 122-00-9 para-methylacetophenone 
• 2386-64-3 ethylmagnesium chloride 
• 539-74-2 Ethyl 3-bromopropionate 
• 60068-20-4 Trimethyl-(1-p-tolyl-cyclopropoxy)-silane 

Downstream Products

• 60068-20-4 Trimethyl-(1-p-tolyl-cyclopropoxy)-silane 
• 1343380-75-5 1-(4'-methylphenyl)-4,4,4-trifluoro-1-butanone 
• 106696-59-7 1-phenyl-6-(p-tolyl)hexane-1,6-dione 
• 5337-93-9 4'-methylpropiophenone 

Relevant academic research and scientific papers

Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C=C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.

Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones

The synthesis of C3-substituted isoindolin-1-ones from oxazolines and cyclopropanols has been achieved with oxazoline as a bifunctional nucleophilic directing group. The reaction proceeds by the cleavage of three chemical bonds and allows the formation of three new chemical bonds, a C-N bond, a C-C bond, and a C-O bond, in a single step.

Aryl Pyrazoles from Photocatalytic Cycloadditions of Arenediazonium

A photocatalytic synthesis of 1,5-diaryl pyrazoles from arenediazoniums and arylcyclopropanols is reported. The reaction proceeded under mild conditions (rt, 20 min) with catalytic [Ru(bpy)3]2+ under blue-light irradiation and exhibited compatibility with several functional groups (e.g., I, SF5, SO2NH2, N3, CN) and perfect levels of regiocontrol. Mechanistic studies (luminescence spectroscopy, CV, DFT, radical trapping, quantum yield determination) documented an initial oxidative quenching of the excited photocatalyst and the operation of a radical-chain mechanism.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

Metal-Free Direct C–H β-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K2S2O8

Direct C–H β-carbonyl alkylation of heteroarenes under metal-, acid- and photo-catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the β-carbonyl alkylation efficiently via K2S2O8-mediated ring-opening of cyclopropanols. The corresponding β-heteroarylated ketones were obtained in moderate to excellent yields and gram-scale experiments further demonstrated the practicality of this synthetic protocol. The readily available reagents, mild and environmentally benign conditions make the method extremely attractive. The reaction mechanism is also proposed.

Ni-Catalyzed Denitrogenative Cross-Coupling of Benzotriazinones and Cyclopropanols: An Easy Access to Functionalized β-Aryl Ketones

A novel Ni-catalyzed denitrogenative cross-coupling between benzotriazinones and cyclopropanols is reported herein. This neoteric reactivity allows for the convenient synthesis of β-(o-amido)aryl ketones from readily available starting materials with good yields (up to 93percent) and general substrate scope.

The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds

A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.

Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones

A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.

Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof

The invention discloses a tetrahydrobenzothiazole-2-acetone oxime derivative, and a preparation method and application thereof. A structural formula is shown in the description. R is any one of the following radical groups: 4-methylphenyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2,5-dimethylphenyl, 3,5-dimethylphenyl, 4-n-propylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,4,5-trimethoxyphenyl, 3-biphenyl, 4-trifluoromethoxyphenyl, 3-fluorophenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, 3-chloro-4-methylphenyl, 3-furyl, 3-thienyl, 2-pyridyl, 4-pyridyl, 2-quinolyl, and 6-quinolyl. The tetrahydrobenzothiazol-2-acetone oxime derivative has relatively high antitumor activity and is suitable for preparing antitumor drugs. The preparationmethod of the derivative has the characteristics of cheap and readily available raw materials, short steps, and high reaction efficiency.

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations

The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.