150668-38-5

Basic information

• Product Name: CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE
• Synonyms: CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE
• CAS NO: 150668-38-5
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• Mol File: 150668-38-5.mol

Chemical Properties

• Boiling Point: 285.3°C at 760 mmHg
• Flash Point: 118.7°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0.00283mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE(150668-38-5)
• EPA Substance Registry System: CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE(150668-38-5)

Safety Data

• Hazardous Substances Data: 150668-38-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE serves as a crucial building block in the synthesis of an array of pharmaceuticals and agrochemicals. Its distinctive structure and reactivity make it an essential component in creating new and effective compounds for these industries.
Used in Flavoring and Fragrance Industries:
CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE also finds application as a flavoring agent or fragrance in the food and cosmetic industries. Its unique chemical properties allow it to impart specific scents or tastes to products, enhancing their appeal to consumers.
Used in Organic Synthesis and Material Science:
CYCLOPROPYL 3,5-DIMETHYLPHENYL KETONE's versatile nature extends to its use in organic synthesis and material science. It plays a role in the development of new materials and chemical processes, contributing to advancements in these fields.

InChI:InChI=1/C12H14O/c1-8-5-9(2)7-11(6-8)12(13)10-3-4-10/h5-7,10H,3-4H2,1-2H3

Upstream product

• 150668-36-3 4-chloro-1-(3,5-dimethylphenyl)butan-1-one 
• 556-96-7 5-bromo-1,3-xylene 
• 147356-78-3 cyclopropanecarboxylic acid N-methoxy-N-methylamide 
• 5500-21-0 cyclopropropanecarbonitrile 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 

Downstream Products

• 765312-46-7 2-(3',5'-dimethylphenyl)-1-pyrroline 

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.

B(C6F5)3-Catalyzed Hydrosilylation of Vinylcyclopropanes

A hydrosilylation of vinylcyclopropanes (VCPs) catalyzed by the strong boron Lewis acid B(C6F5)3 is reported. For the majority of VCPs, little or no ring opening of the cyclopropyl unit is observed. Conversely, for VCPs with bulky R groups, such as ortho-substituted aryl rings or branched alkyl residues, ring opening is the exclusive reaction pathway. This finding is explained by the thwarted hydride delivery to a sterically shielded, β-silicon-stabilized cyclopropylcarbinyl cation intermediate.

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.).

Precise Control of the Formation of a Covalent and an Ionic Bond in Carbocation-Carbanion Combination Reactions

The electronic effect on the selectivity of covalent or ionic bond formation was examined for the reaction of Kuhn's anion 1(1-) (C67H39(1-); tris(7H-dibenzofluorenylidenemethyl)methide ion) and 1-aryl-2,3-dicyclopropylcyclopropenylium ions.The carbocation stability was progressively changed by varying the substituent on the phenyl ring, while the steric effect was kept essentially unchanged.The cations having the p-chlorophenyl (2a(1+)), phenyl (2b(1+)), m-methylphenyl (2c(1+)), or m,m'-dimethylphenyl (2d(1+)) group gave a covalent product, whereas a carbocation-carbanion salt was obtained from the cations having the p-methylphenyl (2e(1+)) or p-methoxyphenyl (2f(1+)) group.The reduction potentials Ered of the cations, as determined by cyclic voltammetry, showed that the formation of the covalent or ionic product is switched by a small difference in stability ( 0.4 kcal/mol) between 2d(1+) and 2e(1+).In chloroform, the salts 1(1-)2e(1+) and 1(1-)2f(1+) were transformed into covalent forms 1-2e and 1-2f, which can exist only in solution.When 1-(2a-d) and 1(1-)2e,f(1+) were dissolved in DMSO, equilibrium between a covalent compound and ions was established.A plot of the free energy of heterolysis ΔG0het for 1-(2a-f) against the Ered of the corresponding cations 2a-f(1+) showed that ΔG0het decreases as the cation is more stabilized.The heterolysis in DMSO was shown to be enhanced by ca. 13 kcal/mol both by the steric congestion in the covalent molecules and the stabilization of the cyclopropenylium ions by solvation.