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

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

Uses

Used in Pharmaceutical Industry:
Cyclopropylmethyl phenyl ketone is used as a building block for the preparation of pharmaceuticals, contributing to the development of various medications due to its unique structural properties.
Used in Agrochemical Industry:
Cyclopropylmethyl phenyl ketone also serves as a building block in the synthesis of agrochemicals, playing a role in the creation of substances that help protect and enhance crop yields.
Used in Fragrance and Flavor Industry:
Cyclopropylmethyl phenyl ketone is employed as an intermediate in the production of fragrances and flavors, adding to the complexity and variety of scents and tastes in various products.
Used in Organic Synthesis:
As a key intermediate, cyclopropylmethyl phenyl ketone is utilized in various organic synthesis reactions, further expanding its applications across different industries that rely on organic chemistry for product development.

Upstream product

• 33574-02-6 cyclopropylmethyl iodide 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 6542-60-5 2-cyclopropylacetonitrile 
• 763-13-3 but-3-en-1-yltrimethylsilane 
• 98-88-4 benzoyl chloride 
• 82994-41-0 β-tributylstannylpropionaldehyde 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 36635-36-6 3-butenyltributylstannane 
• 100-58-3 phenylmagnesium bromide 
• 54322-65-5 cyclopropylacetyl chloride 
• 71-43-2 benzene 
• 37904-33-9 (2-cyclopropylethyl)benzene 
• 84040-29-9 2-bromo-2-cyclopropyl-1-phenylethan-1-one 
• 75-11-6 diiodomethane 

Downstream Products

• 18729-51-6 2-cyclopropyl-1-phenyl-1-ethanol 
• 84040-29-9 2-bromo-2-cyclopropyl-1-phenylethan-1-one 
• 903904-06-3 2-cyclopropyl-1,3-diphenyl-1,3-propanedione 
• 1443367-87-0 2-cyclopropyl-1-phenylethanone oxime 
• 1443368-13-5 1-(2-cyclopropyl-1-phenylethylidene)-2-phenylhydrazine 
• 1443368-14-6 1-(2-cyclopropyl-1-phenylethylidene)-2-phenylhydrazine 
• 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.

Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis

Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is developed based on the coupling of α-keto sulfoxonium ylides with cyclopropanols. The mild protocol features a broad substrate scope (47 examples) and a high product yield (up to 99%). Mechanistic studies argue against a radical pathway and support a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.

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.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Method for hydrogenolysis of halides

The invention discloses a method for hydrogenolysis of halides. The invention discloses a preparation method of a compound represented by a formula I. The preparation method comprises the following step: in a polar aprotic solvent, zinc, H2O and a compound represented by a formula II are subjected to a reaction as shown in the specification, wherein X is halogen; Y is -CHRR or R; hydrogenin H2O exists in the form of natural abundance or non-natural abundance. According to the preparation method, halide hydrogenolysis can be simply, conveniently and efficiently achieved through a simple and mild reaction system, and good functional group compatibility and substrate universality are achieved.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.

Electrochemically Oxidative α-C-H Functionalization of Ketones: A Cascade Synthesis of α-Amino Ketones Mediated by NH4I

An efficient electrochemical protocol for the synthesis of α-amino ketones via the oxidative cross-dehydrogenative coupling of ketones and secondary amines has been developed. The electrochemistry performs in a simple undivided cell using NH4I

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.

A chemoselective α-aminoxylation of aryl ketones: a cross dehydrogenative coupling reaction catalysed by Bu4NI

Tetrabutyl ammonium iodide (TBAI) catalyzed α-aminoxylation of ketones using aq. TBHP as an oxidant has been accomplished. We have shown that the CDC (cross dehydrogenative coupling) reactions of ketones with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI), N-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) lead to the corresponding oxygenated products in good to moderate yields. The application of this method has been demonstrated by transforming a few coupled products into synthetically useful intermediates and products.