14272-73-2

Basic information

• Product Name: 5,5-Dimethyl-2-hexanone
• Synonyms: 5,5-Dimethyl-2-hexanone;5,5-Dimethylhexan-2-one
• CAS NO: 14272-73-2
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21204
• Mol File: 14272-73-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,5-Dimethyl-2-hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-Dimethyl-2-hexanone(14272-73-2)
• EPA Substance Registry System: 5,5-Dimethyl-2-hexanone(14272-73-2)

Safety Data

• Hazardous Substances Data: 14272-73-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 3777, 1971 DOI: 10.1021/ja00744a043

Upstream product

• 930-68-7 cyclohexenone 
• 201230-82-2 carbon monoxide 
• 594-19-4 tert.-butyl lithium 
• 3522-94-9 2,2,5-trimethylhexane 
• 67-56-1 methanol 
• 97-94-9 triethyl borane 
• 558-17-8 tert-Butyl iodide 
• 78-94-4 methyl vinyl ketone 
• 503-17-3 dimethylacetylene 
• 558-37-2 tert-butylethylene 
• 100-52-7 benzaldehyde 
• 104-55-2 3-phenyl-propenal 
• 590-73-8 2,2-dimethylhexane 

Relevant articles and documents

Reactions at interfaces: Oxygenation of n-butyl ligands anchored on silica surfaces with methyl(trifluoromethyl)dioxirane

The oxygenation of n-butyl and n-butoxy chains bonded to silica with methyl(trifluoromethyl)dioxirane (1) revealed the ability of the silica matrix to release electron density toward the reacting C2-H σ-bond through the Si-C1 and Si-O1 σ-bonds connecting the alkyl chain to the surface (silicon β-effect). The silica surface impedes neither the alkyl chain adopting the conformation required for the silicon β-effect nor dioxirane 1 approaching the reactive C2 methylene group. Reaction regioselectivity is insensitive to changes in the solvation of the reacting system, the location of organic ligands on the silica surface, and the H-bonding character of the silica surface. Reaction rates are faster for those organic ligands either within the silica pores or bonded to hydrophilic silica surfaces, which evidence the enhanced molecular dynamics of confined dioxirane 1 and the impact of surface phenomena on the reaction kinetics. The oxygenation of n-butyl and n-butoxy chains carrying trimethylsilyl, trimethoxysilyl, and tert-butyl groups with dioxirane 1 under homogeneous conditions confirms the electronic effects of the silyl substituents and the consequences of steric hindrance on the reaction rate and regioselectivity. Orthosilicic acid esters react preferentially at the methylene group adjacent to the oxygen atom in clear contrast with the reactivity of the carboxylic or sulfonic acid alkyl esters, which efficiently protect this position toward oxidation with 1 (Figure presented).

Tandem catalytic triple-bond cleavage of alkyne in association with aldehyde, alkene, and water

In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, al-kene, and H2O under catalyst mixtures of Rh(I), 2-amino-3-picoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting ,α,β-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis. Georg Thieme Verlag Stuttgart.

FACILE ROUTES TO BORON ENOLATES. Et3B-MEDIATED REFORMATSKY TYPE REACTION AND THREE COMPONENTS COUPLING REACTION OF ALKYL IODIDES, METHYL VINYL KETONE, AND CARBONYL COMPOUNDS

Reaction of α-bromoketones with Ph3SnH in the presence of Et3B provides boron enolates which react with carbonyl compounds to give β-hydroxyketones in good yields.Et3B-induced Reformatsky type reaction of α-iodoketones with an aldehyde or ketone proceeds without Ph3SnH.