7143-76-2

Basic information

• Product Name: cyclopropyl p-tolyl ketone
• Synonyms: cyclopropyl p-tolyl ketone;(4-Methylphenyl)cyclopropyl ketone;4-Methylphenylcyclopropyl ketone;Einecs 230-445-8
• CAS NO: 7143-76-2
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• EINECS: 230-445-8
• Mol File: 7143-76-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 261 °C at 760 mmHg
• Flash Point: 106.2 °C
• Appearance: /
• Density: 1.093 g/cm³
• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: cyclopropyl p-tolyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopropyl p-tolyl ketone(7143-76-2)
• EPA Substance Registry System: cyclopropyl p-tolyl ketone(7143-76-2)

Safety Data

• Hazardous Substances Data: 7143-76-2(Hazardous Substances Data)

Usage

General Description

Cyclopropyl p-tolyl ketone, also known as cPK, is a complex organic compound containing a cyclopropyl group (a three-carbon ring), a p-tolyl group (a phenyl ring with a methyl substitute at the para-position), and a ketone group (a carbon-oxygen double bond). Chemically speaking, cyclopropyl p-tolyl ketone is part of the aromatic ketones group. In general, ketones are often used in various industries due to their reactive carbonyl group, including the pharmaceutical, agricultural, and perfume industry, among others. Specifically, aromatic ketones like cyclopropyl p-tolyl ketone have potential uses in synthesis due to the reactivity of not only their carbonyl group, but also due to their aromatic ring.

InChI:InChI=1/C11H12O/c1-8-2-4-9(5-3-8)11(12)10-6-7-10/h2-5,10H,6-7H2,1H3

Upstream product

• 38425-26-2 4-chloro-1-(4-methylphenyl)butan-1-one 
• 7732-18-5 water 
• 106-38-7 para-bromotoluene 
• 147356-78-3 cyclopropanecarboxylic acid N-methoxy-N-methylamide 
• 5720-05-8 4-methylphenylboronic acid 
• 5500-21-0 cyclopropropanecarbonitrile 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 29480-08-8 1-(4-methylphenyl)cyclobutan-1-ol 
• 73335-19-0 Cyclopropanecarboselenoic acid Se-phenyl ester 
• 108-88-3 toluene 
• 624-31-7 4-tolyl iodide 
• 13885-13-7 2-cyclopropyl-2-oxoacetic acid 
• 75-89-8 2,2,2-trifluoroethanol 
• 67-56-1 methanol 

Downstream Products

• 10507-12-7 1-((E)-1-Cyclopropyl-propenyl)-4-methyl-benzene 
• 10507-13-8 1-((Z)-1-Cyclopropyl-propenyl)-4-methyl-benzene 
• 1429308-61-1 9a-(p-tolyl)-7,8,9,9a-tetrahydrothieno[2,3-g]indolizin-5(4H)-one 
• 7166-40-7 4-Chlor-1-(4-fluorphenyl)-(4-tolyl)-1-buten 
• 35981-66-9 (4-Bromomethyl-phenyl)-cyclopropyl-methanone 
• 15620-28-7 1-(1-cyclopropylvinyl)-4-methylbenzene 
• 101552-29-8 1-methyl-4-(1-phenylbuta-1,3-dienyl)benzene 
• 93874-11-4 4,4'-(buta-1,3-diene-1,1-diyl)bis(methylbenzene) 
• 1355648-48-4 C₁₅H₁₈O 
• 1190963-35-9 (Z)-1-(4-methylphenyl)-1-triethylsiloxy-1-butene 
• 1140910-86-6 1-(4-methylphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-butanone 
• 50664-75-0 Trisamin 
• 50829-28-2 2,3-Bis-(4-cyclopropanecarbonyl-phenyl)-propionic acid 
• 50664-69-2 Isopropyl-p-(cyclopropylcarbonyl)phenylacetat 

Relevant articles and documents

Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration

A transition-metal-free (5+1) cycloaddition of aryl-substituted vinylcyclopropanes (VCPs) and hydrosilanes to afford silacyclohexanes is reported. Catalytic amounts of the trityl cation initiate the reaction by hydride abstraction from the hydrosilane, and further progress of the reaction is maintained by self-regeneration of the silylium ions. The new reaction involves a [1,2] migration of an aryl group, eventually furnishing 4- rather than 3-aryl-substituted silacyclohexane derivatives as major products. Various control experiments and quantum-chemical calculations support a mechanistic picture where a silylium ion intramolecularly stabilized by a cyclopropane ring can either undergo a kinetically favored concerted [1,2] aryl migration/ring expansion or engage in a cyclopropane-to-cyclopropane rearrangement.

Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition

A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.

Mild Ring Contractions of Cyclobutanols to Cyclopropyl Ketones via Hypervalent Iodine Oxidation

An iodine-mediated oxidative ring contraction of cyclobutanols has been developed. The reaction allows the synthesis of a wide range of aryl cyclopropyl ketones under mild and eco-friendly conditions. A variety of functional groups including aromatic or alkyl halides, ethers, esters, ketones, alkenes, and even aldehydes are nicely tolerated in the reaction. This is in contrast with traditional synthetic approaches for which poor functional group tolerance is often a problem. The practicality of the method is also highlighted by the tunability of iodine oxidation system. Specifically, combining the iodine(III) reagent with an appropriate base allows the reaction to accommodate a range of challenging electron-rich arene substrates. The facile scalability of this reaction is also exhibited herein. (Figure presented.).