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 
• 91909-17-0 1-cyclopropyl-1-phenyl-3-butyn-1-ol 
• 116195-48-3 ethyl ester of 1-benzoylcyclopropane-1-carboxylic acid 
• 14114-02-4 1-Phenyl-3-cyclopropyl-aceton 
• 825-76-3 α-cyclopropylstyrene 
• 56061-45-1 (Phenylcyclopropylmethylene)cyclopropane 
• 14902-13-7 1.2-Dicyclopropyl-1-phenyl-aethylen 
• 65488-05-3 4-iodobutyrophenone 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 23459-38-3 1-phenylcyclopropylmethylamine 
• 65045-43-4 trans-1,2-dicyclopropylstilbene 
• 5680-48-8 cis-1,4-Dichlor-1-phenyl-but-1-en 
• 5680-49-9 1cis.4-Dichlor-1trans-phenyl-buten-⁽¹⁾ 
• 772-30-5 cyclopropylphenyldiazomethane 

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

Catalytic Aerobic Oxidation of Alkenes with Ferric Boroperoxo Porphyrin Complex; Reduction of Oxygen by Iron Porphyrin

We herein describe the development of a mild and selective catalytic aerobic oxidation process of olefins. This catalytic aerobic oxidation reaction was designed based on experimental and spectroscopic evidence assessing the reduction of atmospheric oxygen using a ferric porphyrin complex and pinacolborane to form a ferric boroperoxo porphyrin complex as an oxidizing species. The ferric boroperoxo porphyrin complex can be utilized as an in-situ generated intermediate in the catalytic aerobic oxidation of alkenes under ambient conditions to form oxidation products that differ from those obtained using previously reported ferric porphyrin catalysis. Moreover, the mild reaction conditions allow chemoselective oxidation to be achieved.

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 comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following 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 reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

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):