3481-02-5

Basic information

• Product Name: Cyclopropyl phenyl ketone
• Synonyms: Methanone,cyclopropylphenyl-;Phenyl cyclopropyl ketone;BENZOYLCYCLOPROPANE;CYCLOPROPYL PHENYL KETONE;CYCLOPROPYL-PHENYL-METHANONE;Cyclopropylphenylketone,97%;Cyclopropyl phenyl k;Cyclopropyl phenyl ketone 98%
• CAS NO: 3481-02-5
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• EINECS: 222-458-2
• Product Categories: Cyclopropanes;Simple 3-Membered Ring Compounds
• Mol File: 3481-02-5.mol
• Article Data: 176

Chemical Properties

• Melting Point: 7-9 °C(lit.)
• Boiling Point: 121-123 °C15 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: clear colourless to light yellow liquid
• Density: 1.058 g/mL at 25 °C(lit.)
• Vapor Density: 5 (vs air)
• Vapor Pressure: 0.034mmHg at 25°C
• Refractive Index: n20/D 1.553(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water.
• BRN: 1860145
• CAS DataBase Reference: Cyclopropyl phenyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropyl phenyl ketone(3481-02-5)
• EPA Substance Registry System: Cyclopropyl phenyl ketone(3481-02-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3481-02-5(Hazardous Substances Data)

Usage

Description

Cyclopropyl phenyl ketone is an organic compound characterized by its clear colorless to light yellow liquid appearance. It features a cyclopropane ring attached to a phenyl group, with a carbonyl group (C=O) connecting the two structures.

Uses

Used in Chemical Synthesis:
Cyclopropyl phenyl ketone is used as a starting reagent for the preparation of α-cyclopropylstyrene through the Wittig reaction in dimethyl sulfoxide. This reaction is a widely employed method for the synthesis of alkenes, which are essential components in various chemical and pharmaceutical applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Cyclopropyl phenyl ketone serves as a starting reagent during the (Z)-titanium enolate formation from cyclopropyl ketones via TiCl4-n-Bu4NI-induced ring-opening reaction. This process is crucial for the synthesis of various pharmaceutical compounds, as it allows for the creation of complex molecular structures with potential therapeutic properties.
Used in Organic Chemistry Research:
Cyclopropyl phenyl ketone is also utilized in organic chemistry research, where it can be employed to study the reactivity and properties of cyclopropane rings and their influence on the overall chemical behavior of the molecule. This research can lead to the development of new synthetic methods and applications in various fields, including materials science and drug discovery.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 2921, 1980 DOI: 10.1021/jo01302a038Tetrahedron Letters, 16, p. 4389, 1975 DOI: 10.1016/S0040-4039(00)91132-8

InChI:InChI=1/C10H10O/c11-10(9-6-7-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 825-76-3 α-cyclopropylstyrene 
• 24070-52-8 4-bromo-1-phenyl-1-butanone 
• 20127-68-8 (cyclopropylphenylmethylene)amine 
• 79172-43-3 1-benzoylcyclopropanecarboxylic acid 
• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 71-43-2 benzene 
• 5500-21-0 cyclopropropanecarbonitrile 
• 74-89-5 methylamine 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 41893-65-6 (1-bromo-1-phenylmethylene)cyclopropane 
• 64-17-5 ethanol 
• 87639-40-5 4-phenyl-3-butyn-1-yl trifluoromethanesulfonate 
• 87639-41-6 4-p-tolylbut-3-yn-1-yl triflate 

Downstream Products

• 5558-04-3 1-cyclopropyl-1-phenylethanol 
• 5785-66-0 cyclopropyl diphenyl carbinol 
• 58688-34-9 (1-benzylcyclopropyl)-(phenyl)methanone 
• 24070-52-8 4-bromo-1-phenyl-1-butanone 
• 1667-00-1 benzylcyclopropane 
• 1007-03-0 1-phenyl-1-cyclopropylmethanol 
• 26921-44-8 (1-methylcyclopropyl)phenylketone 
• 614-14-2 1-Phenyl-1-butanol 
• 5680-51-3 cyclopropyl-(3-nitrophenyl)methanone 
• 7555-72-8 cyclopropyl(phenyl)methanone oxime 
• 39755-06-1 4-Oxo-4-phenyl-1-acetoxybutane 
• 91909-17-0 1-cyclopropyl-1-phenyl-3-butyn-1-ol 
• 75343-45-2 cyclopropyl-phenyl ketone-(2,4-dinitro-phenylhydrazone) 
• 116195-48-3 ethyl ester of 1-benzoylcyclopropane-1-carboxylic acid 

Relevant articles and documents

Oxygen acidity of ring methoxylated 1,1-diarylalkanol radical cations bearing α-cyclopropyl groups. The competition between O-neophyl shift and C-cyclopropyl β-scission in the intermediate 1,1-diarylalkoxyl radicals

A product and time-resolved kinetic study on the reactivity of the radical cations generated from cyclopropyl(4-methoxyphenyl)phenylmethanol (1) and cyclopropyl[bis(4-methoxyphenyl)]methanol (2) has been carried out in aqueous solution. In acidic solution, 1.+ and 2.+ display very low reactivities toward fragmentation, consistent with the presence of groups at Cα (aryl and cyclopropyl) that after Cα-C β bond cleavage would produce relatively unstable carbon-centered radicals. In basic solution, 1.+ and 2.+ display oxygen acidity, undergoing -OH-induced deprotonation from the α-OH group, leading to the corresponding 1,1-diarylalkoxyl radicals 1r. and 2r., respectively, as directly observed by time-resolved spectroscopy. The product distributions observed in the reactions of 1.+ and 2.+ under these conditions (cyclopropyl phenyl ketone, cyclopropyl(4-methoxyphenyl) ketone, and 4-methoxybenzophenone from 1.+; cyclopropyl(4-methoxyphenyl) ketone and 4,4′- dimethoxybenzophenone from 2.+) have been rationalized in terms of a water-induced competition between O-neophyl shift and C-cyclopropyl β-scission in the intermediate 1,1-diarylalkoxyl radicals 1r. and 2r..

Aquacatalytic aerobic oxidation of benzylic alcohols with a self-supported bipyridyl-palladium complex

The aerobic oxidation of alcohols was promoted in water under atmospheric molecular oxygen by a readily recyclable self-supported bipyridyl-palladium polymeric complex, which was prepared via construction of a metal-organic framework (MOF) of a bipyridyl-palladium complex bearing carboxylic groups and a copper(II) linker. Copyright

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):