22376-51-8

Basic information

• Product Name: 2-((Dimethylamino)Methyl)-6-Methylcyclohexanone
• CAS NO: 22376-51-8
• Molecular Weight: 169.15
• Mol File: 22376-51-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-((Dimethylamino)Methyl)-6-Methylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((Dimethylamino)Methyl)-6-Methylcyclohexanone(22376-51-8)
• EPA Substance Registry System: 2-((Dimethylamino)Methyl)-6-Methylcyclohexanone(22376-51-8)

Safety Data

• Hazardous Substances Data: 22376-51-8(Hazardous Substances Data)

Usage

Structure

Cyclohexanone derivative with a dimethylamino group and a methyl group on the cyclohexane ring

Usage

As a starting material in the synthesis of various pharmaceutical and organic compounds, intermediate in the production of fragrances and flavors, and studied for potential application in organic synthesis and medicinal chemistry

Unique features

Unique structure and reactivity

Upstream product

• 50-00-0 formaldehyd 
• 583-60-8 2-Methylcyclohexanone 
• 124-40-3 dimethyl amine 
• 51-80-9 bis-(dimethylamino)methane 
• 19980-33-7 6-methyl-1-trimethylsiloxycyclohex-1-ene 
• 33797-51-2 eschenmoser's salt 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 107046-65-1 2-[1-Dimethylamino-meth-(E)-ylidene]-6-methyl-cyclohexanone 

Relevant articles and documents

γ-Methylenation of α,β-unsaturated ketones

γ-Methylene derivatives of α,β-unsaturated ketones are obtained readily by a one-pot procedure exploiting the reaction of O-silylated dienolates with commercially available formaldehyde N,N-dimethyliminium chloride in anhydrous N,N-dimethylformamide, in s

THE SYNTHESIS OF MANNICH BASES FROM KETONES AND ESTERS VIA ENAMINONES.

The reactions of a series of activated methylene compounds with amide acetals to form high yields of enaminones is described.Further conversion to the Mannich bases via reduction with lithium aluminium hydride is also covered.

Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and N,N,N',N'-Tetramethylmethanediamine

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH2ClI) and N,N,N',N'-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperatute.The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies.The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser's salt ().