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 
• 41902-42-5 tri-tert-butylcarbinol 
• 20818-90-0 p-Nitro-benzoesaeure-1,1-di-tert-butyl-2,2-dimethyl-propylester 
• 29772-39-2 2,2,3,4-tetramethyl-3-pentanol 
• 75-28-5 Isobutane 
• 32579-71-8 2,2,4,4-tetramethyl-3-neopentylpentan-3-ol 
• 4298-71-9 1-chloro-2,2,4,4-tetramethyl-pentan-3-one 
• 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 
• 54440-13-0 2-(1,1-dimethylethyl)-3,3-dimethyl-1-phenylbut-1-ene 
• 3229-31-0 p-nitrophenyl-t-butylaminoxyl 
• 17226-40-3 3-(4'-methoxyphenyl)-2,2,4,4-tetramethylpentan-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.

A reusable unsupported rhenium nanocrystalline catalyst for acceptorless dehydrogenation of alcohols through γ-C-H activation

Rhenium nanocrystalline particles (Re NPs), of 2 nm size, were prepared from NH4ReO4 under mild conditions in neat alcohol. The unsupported Re NPs convert secondary and benzylic alcohols to ketones and aldehydes, respectively, through catalytic acceptorless dehydrogenation (AD). The oxidant- and acceptor-free neat dehydrogenation of alcohols to obtain dihydrogen gas is a green and atom-economical process for making carbonyl compounds. Secondary aliphatic alcohols give quantitative conversion and yield. Transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), Re K-edge X-ray absorption near-edge structure (XANES), and X-ray absorption fine structure (EXAFS) data confirmed the characterization of the Re NPs as metallic rhenium with surface oxidation to rhenium(IV) oxide (ReO2). Isotope labeling experiments revealed a novel γ-CH activation mechanism for AD of alcohols. Active particles: A rhenium nanoparticle (Re NP) catalyst is generated from NH4ReO4 under mild solution conditions in neat 3-octanol at 180°C. The resulting Re NPs catalyze acceptorless dehydrogenation of alcohols through a novel C-H activation pathway, and are fully recyclable. Copyright

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.