58249-45-9

Usage

Class of compound

Aromatic hydrocarbon derivative

Groups attached

tert-butyl group, cyclopropylmethyl group

Common uses

Synthesis of various organic molecules, pharmaceuticals

Molecular weight

188.31 g/mol

Potential applications

Pharmaceutical industry

Basis for potential applications

Structural properties, potential biological activities

Upstream product

• 172477-52-0 2-(4-tert-butylbenzyl)-1,3-propanediol 
• 37765-76-7 2-(4-tert-butylbenzyl)diethylmalonate 
• 172477-58-6 5-(4-tert-butylbenzyl)-1,3,2-dioxathiane-2,2-dioxide 
• 4333-56-6 cyclopropyl bromide 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 

Downstream Products

• 3282-56-2 4-tert-butylnitrobenzene 
• 1412494-26-8 5-(4-tert-butylbenzyl)-4,5-dihydroisoxazole 

Relevant academic research and scientific papers

Transformations of para-substituted benzylcyclopropanes, allylbenzenes, and diphenylmethanes under nitration with nitric acid in acetic anhydride

Electrophilic nitration of benzylcyclopropanes, allylbenzenes, and diphenylmethanes containing ortho, para-orienting substituents in the para position of the benzene ring results mainly in replacement of the cyclopropylmethyl, allyl, or benzyl group, respectively (ipso substitution). The nitration of 4-cyclopropylallylbenzene is not accompanied by nitrodealkylation, and the products are only 2- and 3-nitro-4-cyclopropylallylbenzenes.

Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates

The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.