564-04-5

Basic information

• Product Name: 2,2-DIMETHYL-3-PENTANONE
• Synonyms: 2,2-Dimethyl-3-oxopentane, Ethyl tert-butyl ketone;4,4-Dimethyl-3-pentanone;NSC 244941;t-Butyl ethyl ketone;3-Pentanone,2,2-dimethyl-;Ethyl tert-butyl ketone;tert-Butyl Ethyl ketone;tert-butylethylketone
• CAS NO: 564-04-5
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.19
• Mol File: 564-04-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: -45°C
• Boiling Point: 124.85°C
• Flash Point: 22.4 °C
• Appearance: /
• Density: 0.808
• Vapor Pressure: 10.8mmHg at 25°C
• Refractive Index: 1.4028
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,2-DIMETHYL-3-PENTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-3-PENTANONE(564-04-5)
• EPA Substance Registry System: 2,2-DIMETHYL-3-PENTANONE(564-04-5)

Safety Data

• Hazardous Substances Data: 564-04-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless transparent liquid

InChI:InChI=1/C7H14O/c1-5-6(8)7(2,3)4/h5H2,1-4H3

Upstream product

• 540-84-1 2,2,4-trimethylpentane 
• 87944-70-5 2,3-dimethyl-2,3-epoxypentane 
• 78-93-3 butanone 
• 333-27-7 methyl trifluoromethanesulfonate 
• 60-29-7 diethyl ether 
• 677-22-5 tert-butylmagnesium chloride 
• 79-03-8 propionyl chloride 
• 115569-84-1 4-ethyl-4-hydroxy-5,5-dimethyl-hexan-3-one 
• 117800-25-6 (Z)-carbonyl(η1-O-4,4-dimethyl-1-oxy-2-pentene){bis(trimethylphosphine)}rhodium(I) 
• 100-19-6 (4-nitrophenyl)ethanone 
• 74-88-4 methyl iodide 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 4916-82-9 N-cyclohexyl-2,2-dimethylpropanamide 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 36677-29-9 (4SR,5SR)-5-hydroxy-5-phenyl-2,2,4-trimethyl-3-pentanone 
• 28495-73-0 tert-Butylethylketon-tosylhydrazon 
• 93292-03-6 erythro-5-hydroxy-2,4,4-trimethyl-7-phenylheptan-3-one 
• 197074-51-4 (4R,5R)-5-Hydroxy-2,2,4-trimethyl-7-phenyl-heptan-3-one 
• 72658-36-7 erythro-5-hydroxy-2,2,4-trimethyl-6-phenylhexan-3-one 
• 93772-96-4 (1S,2R)-1-(4-Chloro-phenyl)-1-hydroxy-2,4,4-trimethyl-pentan-3-one 
• 93772-96-4 (1R,2S)-1-(4-Chloro-phenyl)-1-hydroxy-2,4,4-trimethyl-pentan-3-one 
• 93772-96-4 (1R,2R)-1-(4-Chloro-phenyl)-1-hydroxy-2,4,4-trimethyl-pentan-3-one 
• 75245-22-6 (Z)-3,4-Diethyl-2,2,5,5-tetramethyl-3-hexen 
• 75245-21-5 (E)-3,4-Diethyl-2,2,5,5-tetramethyl-3-hexen 
• 120362-92-7 (Z)-3-Ethyl-2,2,5,5-tetramethyl-3-hexen 
• 120362-93-8 (E)-3 Ethyl-2,2,5,5-tetramethyl-3-hexen 
• 40794-97-6 threo phenyl-4 trimethyl-5,7,7 octanedione-2,6 
• 40794-97-6 erythro phenyl-4 trimethyl-5,7,7 octanedione-2,6 

Relevant articles and documents

Reactivity of Lithium β-Ketocarboxylates: The Role of Lithium Salts

Lithium β-ketocarboxylates 1(COOLi), prepared by the reaction of lithium enolates 2(Li+) with carbon dioxide, readily undergo decarboxylative disproportionation in THF solution unless in the presence of lithium salts, in which case they are indefinitely stable at room temperature in inert atmosphere. The availability of stable THF solutions of lithium β-ketocarboxylates 1(COOLi) in the absence of carbon dioxide allowed reactions to take place with nitrogen bases and alkyl halides 3 to give α-alkyl ketones 1(R) after acidic hydrolysis. The sequence thus represents the use of carbon dioxide as a removable directing group for the selective monoalkylation of lithium enolates 2(Li+). The roles of lithium salts in preventing the disproportionation of lithium β-ketocarboxylates 1(COOLi) and in determining the course of the reaction with bases and alkyl halides 3 are discussed.

Dialkylation of Ketone Dianions

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Synthesis of η1 Oxygen-Bound Rhodium Enolates. Applications to Catalytic Aldol Chemistry

Oxygen-bound rhodium enolate complexes are prepared by metathesis of carbonylbis(phosphine)rhodium(I) halides and potassium enolates, 3-6.Rhodium enolates of acetophenone (7), propiophenone (9), ethyl mesityl ketone (10), and ethyl tert-butyl ketone (11) were prepared and fully characterized.Complex 11 condenses with benzaldehyde under a variety of conditions to produce isolable rhodium aldolate complex 12.Cleavage of 12 with trimethylsilyl chloride yields aldol silyl ether and rhodium chloride.Similar treatment of 12 with an enol silane affords the aldol silylether and a rhodium enolate.A catalytic aldol reaction involving enol silanes, silylketene acetals, and benzaldehyde under rhodium catalysis is presented.Deuterium, phosphorus, and carbon NMR were used to demonstrate the intermediacy of rhodium enolates and aldolates in the aldol process and to elucidate the gross mechanistic features of the catalytic cycle.