7143-76-2

Basic information

• Product Name: cyclopropyl p-tolyl ketone
• Synonyms: cyclopropyl p-tolyl ketone;(4-Methylphenyl)cyclopropyl ketone;4-Methylphenylcyclopropyl ketone;Einecs 230-445-8
• CAS NO: 7143-76-2
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• EINECS: 230-445-8
• Mol File: 7143-76-2.mol

Chemical Properties

• Boiling Point: 261 °C at 760 mmHg
• Flash Point: 106.2 °C
• Appearance: /
• Density: 1.093 g/cm³
• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: cyclopropyl p-tolyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopropyl p-tolyl ketone(7143-76-2)
• EPA Substance Registry System: cyclopropyl p-tolyl ketone(7143-76-2)

Safety Data

• Hazardous Substances Data: 7143-76-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclopropyl p-tolyl ketone is used as an intermediate in the synthesis of various pharmaceutical compounds due to the reactivity of its carbonyl and aromatic ring groups. This allows for the creation of a diverse range of drug molecules with potential therapeutic applications.
Used in Agricultural Industry:
In the agricultural sector, cyclopropyl p-tolyl ketone is used as a chemical intermediate for the production of agrochemicals, such as pesticides and herbicides. Its reactivity enables the development of effective compounds that can protect crops from pests and diseases.
Used in Perfume Industry:
Cyclopropyl p-tolyl ketone is utilized as a fragrance ingredient in the perfume industry. The aromatic nature of the compound contributes to the creation of unique and complex scents, enhancing the overall appeal of perfumes and fragrances.
Used in Synthesis:
Cyclopropyl p-tolyl ketone is used as a versatile building block in organic synthesis, allowing for the creation of a wide array of chemical compounds. Its reactivity with both the carbonyl and aromatic ring groups makes it a valuable component in the synthesis of various organic molecules.

InChI:InChI=1/C11H12O/c1-8-2-4-9(5-3-8)11(12)10-6-7-10/h2-5,10H,6-7H2,1H3

Upstream product

• 108-88-3 toluene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 75-89-8 2,2,2-trifluoroethanol 
• 87639-41-6 4-p-tolylbut-3-yn-1-yl triflate 
• 87639-42-7 4-p-tolylbut-3-yn-1-yl tosylate 
• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 38425-26-2 4-chloro-1-(4-methylphenyl)butan-1-one 
• 7732-18-5 water 
• 624-31-7 4-tolyl iodide 
• 13885-13-7 2-cyclopropyl-2-oxoacetic acid 
• 73335-19-0 Cyclopropanecarboselenoic acid Se-phenyl ester 
• 106-38-7 para-bromotoluene 
• 147356-78-3 cyclopropanecarboxylic acid N-methoxy-N-methylamide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 20840-08-8 (E)-4-(4-methylphenyl)but-3-en-1-ol 
• 6552-46-1 4-methylphenylcyclopropylcarbinol 
• 22217-77-2 5-(p-tolyl)-3,4-dihydro-2H-pyrrole 
• 937237-77-9 C₁₃H₁₄O 
• 85157-61-5 1‐(2‐cyclopropylethynyl)‐4‐methylbenzene 
• 1190963-35-9 (Z)-1-(4-methylphenyl)-1-triethylsiloxy-1-butene 
• 1355648-48-4 C₁₅H₁₈O 
• 1429308-61-1 9a-(p-tolyl)-7,8,9,9a-tetrahydrothieno[2,3-g]indolizin-5(4H)-one 
• 7166-40-7 4-Chlor-1-(4-fluorphenyl)-(4-tolyl)-1-buten 
• 35981-66-9 (4-Bromomethyl-phenyl)-cyclopropyl-methanone 
• 101552-29-8 1-methyl-4-(1-phenylbuta-1,3-dienyl)benzene 

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.).

AZETIDINE COMPOUNDS AS GRP119 MODULATORS FOR THE TREATMENT OF DIABETES, OBESITY, DYSLIPIDEMIA AND RELATED DISORDERS

The present disclosure relates to azetidine compounds. The azetidine compounds are GPR119 modulators and useful for the prevention and/or treatment of diabetes, obesity, dyslipidemia and related disorders. The present disclosure furthermore relates to the use of azetidine compounds as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

DECARBOXYLATIVE CROSS-COUPLING AND APPLICATIONS THEREOF

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. For example, methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate. The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners.

A cascade approach to fused indolizinones through Lewis acid-copper(i) relay catalysis

A relay catalytic cascade process involving Lewis acid triggered ring-opening of cyclopropyl ketones with nitriles, the copper(i)-catalyzed Ritter process, and acid-promoted N-acyliminium ion cyclization is described, which efficiently provides thieno-, furano-, and benzo-indolizinones in moderate to good yields. The Royal Society of Chemistry 2013.

Intermediates useful for the preparation of antihistaminic piperidine derivatives

The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2;n is an integer of from 1 to 5;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; andpharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.