6739-22-6

Basic information

• Product Name: Cyclopropylmethyl phenyl ketone
• Synonyms: Cyclopropylmethyl phenyl ketone;Ethanone, 2-cyclopropyl-1-phenyl-;2-Cyclopropyl-1-Phenylethan-1-One(WX626060);2-CYCLOPROPYL-1-PHENYLETHAN-1-ONE
• CAS NO: 6739-22-6
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• Mol File: 6739-22-6.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 253.536 °C at 760 mmHg
• Flash Point: 101.945 °C
• Appearance: /
• Density: 1.066 g/cm³
• CAS DataBase Reference: Cyclopropylmethyl phenyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropylmethyl phenyl ketone(6739-22-6)
• EPA Substance Registry System: Cyclopropylmethyl phenyl ketone(6739-22-6)

Safety Data

• Hazardous Substances Data: 6739-22-6(Hazardous Substances Data)

Usage

General Description

Cyclopropylmethyl phenyl ketone is a compound with the chemical formula C10H10O. It is an aromatic ketone with a cyclopropylmethyl functional group attached to a phenyl ring. Cyclopropylmethyl phenyl ketone is used in various organic synthesis reactions as a building block for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. It is also employed as an intermediate in the production of fragrances and flavors. The unique structural features of cyclopropylmethyl phenyl ketone make it a valuable and versatile compound in the field of organic chemistry.

Upstream product

• 6542-60-5 2-cyclopropylacetonitrile 
• 18729-51-6 2-cyclopropyl-1-phenyl-1-ethanol 
• 33574-02-6 cyclopropylmethyl iodide 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 98-88-4 benzoyl chloride 
• 37904-33-9 (2-cyclopropylethyl)benzene 
• 84040-29-9 2-bromo-2-cyclopropyl-1-phenylethan-1-one 
• 75-11-6 diiodomethane 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 108-86-1 bromobenzene 
• 54322-65-5 cyclopropylacetyl chloride 
• 71-43-2 benzene 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 1202238-30-9 (Z)-((2-cyclopropyl-1-phenylvinyl)oxy)trimethylsilane 
• 136-60-7 benzoic acid, butyl ester 

Relevant articles and documents

Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu2Mg in Toluene

The treatment of primary or secondary alkyl iodides with sBu2Mg in toluene (25–40 °C, 2–4 h) provided dialkylmagnesiums that underwent various reactions with aldehydes, ketones, acid chlorides or allylic bromides. 3-Substituted secondary cyclohexyl iodides led to all-cis-3-cyclohexylmagnesium reagents under these exchange conditions in a highly stereoconvergent manner. Enantiomerically enriched 3-silyloxy-substituted secondary alkyl iodides gave after an exchange reaction with sBu2Mg stereodefined dialkylmagnesiums that after quenching with various electrophiles furnished various 1,3-stereodefined products including homo-aldol products (99 % dr and 98 % ee). Mechanistic studies confirmed a radical pathway for these new iodine/magnesium-exchange reactions.

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement

Herein, we report a synthesis of medicinally relevant β-ketosulfonamides via a photomediated 1,3-rearrangement of alkenyl sulfamates. This protocol tolerates a wide array of sensitive functional groups including alkenes, alkynes, and nitrogen-based heterocycles. Additionally, this work provides a general approach toward alkenyl sulfamates via a two-step Sulfur(VI) Fluoride Exchange (SuFEx) sequence capitalizing on SO2F2 as a linchpin to efficiently couple readily available ketones and amines without a large excess of either partner.