2936-55-2

Basic information

• Product Name: cyclohexyl o-tolyl ketone
• Synonyms: cyclohexyl o-tolyl ketone;2-Methylphenylcyclohexyl ketone;cyclohexyl-(2-methylphenyl)methanone
• CAS NO: 2936-55-2
• Molecular Formula: C₁₄H₁₈O
• Molecular Weight: 202.29212
• EINECS: 220-915-0
• Mol File: 2936-55-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 311.1°C at 760 mmHg
• Flash Point: 130.5°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0.000577mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: cyclohexyl o-tolyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexyl o-tolyl ketone(2936-55-2)
• EPA Substance Registry System: cyclohexyl o-tolyl ketone(2936-55-2)

Safety Data

• Hazardous Substances Data: 2936-55-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H18O/c1-11-7-5-6-10-13(11)14(15)12-8-3-2-4-9-12/h5-7,10,12H,2-4,8-9H2,1H3

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 110-83-8 cyclohexene 
• 17310-32-6 (CH₃C₆H₄)2Cd 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 108-88-3 toluene 
• 98-89-5 Cyclohexanecarboxylic acid 
• 854447-93-1 C₁₄H₁₈O 
• 1267024-37-2 1-(o-tolyl)cyclohexanecarbaldehyde 
• 933-88-0 ortho-toluoyl chloride 
• 110-82-7 cyclohexane 
• 712-50-5 Cyclohexyl phenyl ketone 
• 75-24-1 trimethylaluminum 
• 73774-44-4 bis(2-methylphenyl)borinic acid 
• 16419-60-6 2-Methylphenylboronic acid 

Downstream Products

• 42071-07-8 N-(Cyclohexyl-o-tolyl-methyl)-formamide 
• 42071-17-0 (Cyclohexyl-o-tolyl-methyl)-methyl-amine 

Relevant articles and documents

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

Abstract A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)2Cl2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides.

Fe-catalyzed regiodivergent [1,2]-shift of α-aryl aldehydes

An Fe-catalyzed conversion of aldehydes to ketones via [1,2]-shift has been developed. This skeletal rearrangement shows a wide substrate scope and chemoselectivity profile while exhibiting an excellent [1,2]-aryl or [1,2]-alkyl shift selectivity that is easily switched by electronic effects.