153198-69-7

Basic information

• Product Name: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)
• Synonyms: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)
• CAS NO: 153198-69-7
• Molecular Formula: C11H12O
• Molecular Weight: 160.21238
• Product Categories: ALDEHYDE
• Mol File: 153198-69-7.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)(153198-69-7)
• EPA Substance Registry System: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)(153198-69-7)

Safety Data

• Hazardous Substances Data: 153198-69-7(Hazardous Substances Data)

Upstream product

• 114095-61-3 (2-p-Tolyl-cyclopropyl)-methanol 
• 97023-67-1 ethyl 2-(4-methylphenyl)cyclopropane-1-carboxylate 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 72228-97-8 methyl trans-2-(p-methyphenyl)cyclopropanecarboxylate 
• 20754-20-5 3-p-tolyl-acrylic acid methyl ester 
• 1866-39-3 trans-p-methylcinnamic acid 
• 114095-61-3 (trans-2-(4-methylphenyl)cyclopropyl)methanol 
• 18456-66-1 (1R*,2R*)-ethyl 2-(p-tolyl)cyclopropanecarboxylate 
• 97585-04-1 ethyl (E)-3-(4-methylphenyl)acrylate 
• 104-87-0 4-methyl-benzaldehyde 
• 1866-39-3 4-methylcinnamic acid 
• 1355061-82-3 C₁₂H₁₅NO₂ 
• 122058-30-4 4-methylcinnamyl alcohol 

Relevant articles and documents

Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives

In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Br?nsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis

Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.