815-24-7

Basic information

• Product Name: HEXAMETHYLACETONE
• Synonyms: 2,2,4,4-TETRAMETHYL-3-PENTANONE;HEXAMETHYLACETONE;DI-TERT-BUTYL KETONE;PIVALONE;(t-C4H9)2CO;2,2,4,4-tetramethyl-3-pentanon;2,2,4,4-Tetramethyl-pentan-3-one;2,2,4,4-tetramethylpentan-3-one
• CAS NO: 815-24-7
• Molecular Formula: C₉H₁₈O
• Molecular Weight: 142.24
• EINECS: 212-419-8
• Mol File: 815-24-7.mol
• Article Data: 38

Chemical Properties

• Melting Point: 152-153
• Boiling Point: 152-153 °C(lit.)
• Flash Point: 91 °F
• Appearance: Clear colorless/Liquid
• Density: 0.824 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.53mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
• BRN: 1701122
• CAS DataBase Reference: HEXAMETHYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXAMETHYLACETONE(815-24-7)
• EPA Substance Registry System: HEXAMETHYLACETONE(815-24-7)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 815-24-7(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Hexamethylacetone is used to prepare di-tert.-butyladamantylcarbinol by reacting with 1-bromo-adamantane.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 4141, 1949 DOI: 10.1021/ja01180a082The Journal of Organic Chemistry, 39, p. 611, 1974 DOI: 10.1021/jo00919a007

General Description

The Microtox EC50 values for 2,2,4,4-tetramethyl-3-pentanone has been reported. The kinetics, stoichiometry and products of the reduction reaction of 2,2,4,4-tetramethyl-3-pentanone using lithium triethylborohydride under standard conditions (tetrahydrofuran, 0°C) has been examined.

InChI:InChI=1/C9H18O/c1-8(2,3)7(10)9(4,5)6/h1-6H3

Upstream product

• 5857-36-3 2,2,4-trimethylpentanone 
• 507-20-0 tertiary butyl chloride 
• 598-98-1 Methyl pivalate 
• 61065-35-8 2,3,4,4-tetramethyl-pentane-2,3-diol 
• 594-19-4 tert.-butyl lithium 
• 15719-64-9 methylammonium carbonate 
• 677-22-5 tert-butylmagnesium chloride 
• 3282-30-2 pivaloyl chloride 
• 565-80-0 2,4-dimethylpentan-3-one 
• 74-88-4 methyl iodide 
• 54396-69-9 Di-tert-butyl thioketone 
• 54396-68-8 3-diazo-2,2,4,4-tetramethylpentane 
• 33581-95-2 tert-butylsulfamyl chloride 
• 35895-37-5 2,4-dimethyl-3-iodopent-2-ene 

Downstream Products

• 5857-69-2 2,2,3,4,4-pentamethyl-3-pentanol 
• 40544-06-7 4-Nitro-benzoic acid 1-tert-butyl-1-(4-chloro-phenyl)-2,2-dimethyl-propyl ester 
• 40544-05-6 Phenyl-di-t-butylcarbinol-p-nitrobenzoat 
• 20818-91-1 3-tert-butyl-2,2,5,5-tetramethyl-3-(4-nitro-benzoyloxy)-hexane 
• 37892-63-0 3-tert-butyl-4,4-dimethyl-1-phenylpent-1-yn-3-ol 
• 2048-07-9 1,2-bis(2-methylphenyl)-1,2-ethanedione 
• 118712-16-6 3-(2,4-Dimethyl-phenyl)-2,2,4,4-tetramethyl-pentan-3-ol 
• 14609-79-1 2,2,4,4-tetramethyl-3-pentanol 
• 41902-42-5 tri-tert-butylcarbinol 
• 63162-57-2 2,2,4,4-tetramethyl-3-(2-methylphenyl)pentan-3-ol 
• 63121-55-1 3-(2,5-Dimethyl-phenyl)-2,2,4,4-tetramethyl-pentan-3-ol 
• 63121-56-2 3-(5-Chloro-2-methyl-phenyl)-2,2,4,4-tetramethyl-pentan-3-ol 
• 63121-53-9 p-Methoxy-o-tolyldi-tert.-butylcarbinol 
• 118712-19-9 2,2,4,4-tetramethyl-3-(2,3,4,5-tetramethylphenyl)pentan-3-ol 

Relevant articles and documents

Dehalogenation of 1,3-diiodotricyclo[3.3.0.03,7]octane: Generation of 1,3dehydrotricyclo[3.3.0.03,7]octane, a 2,5-methano-bridged [2.2.1]propellane

Compounds isolated from the reaction of (±)-1,3-diiodotricy-clo[3.3. 0.03,7]octane with molten sodium or tBuLi suggest the intermediate formation of (±)-1,3-dehydrotricyclo[3.3.0.03,7]octane. Worthy of note is the formation of stereoisomeric bi(5-methylenebicyclo[2.2.1]hept-2- ylidene) derivatives, probably by coupling of two units of (±)-1,3- dehydrotricyclo[3.3.0.03,7]octane of the same or different absolute configuration followed by fragmentation, processes that have been studied by theoretical calculations.

Alcohol oxidation via recyclable hydrophobic ionic liquid-supported IBX

The first ionic hydrophobic liquid-supported 1-hydroxy-1,2-benziodoxole-3(1H)-one-1-oxide (IBX) reagent was prepared for oxidizing alcohols. In this study, a hydrophobic ionic liquid-supported IBX reagent was synthesized and described. This hydrophobic ionic liquid-supported IBX reagent was able to be recovered and used in a recyclable reaction system by re-oxidation and washing.

The retro Grignard addition reaction revisited: The reversible addition of benzyl reagents to ketones

The Grignard addition reaction is known to be a reversible process with allylic reagents, but so far the reversibility has not been demonstrated with other alkylmagnesium halides. By using crossover experiments it has been established that the benzyl addition reaction is also a reversible transformation. The retro benzyl reaction was shown by the addition of benzylmagnesium chloride to di-tert-butyl ketone followed by exchange of both the benzyl and the ketone moiety with another substrate. Similar experiments were performed with phenylmagnesium bromide and tert-butylmagnesium chloride, but in these two cases the Grignard addition reaction did not show any sign of a reverse transformation.

Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes

A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.