30314-44-4

Basic information

• Product Name: tert-Butyl(4-methylphenyl) ketone
• Synonyms: 2,2-Dimethyl-1-(4-methylphenyl)-1-propanone;SaH-50-283;tert-Butyl(4-methylphenyl) ketone;α,α,4'-Trimethylpropiophenone;2,2,4'-TRIMETHYLPROPIOPHENONE;2,2-DIMETHYL-1-(4-METHYLPHENYL)PROPAN-1-ONE
• CAS NO: 30314-44-4
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.26
• Mol File: 30314-44-4.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 254.5°Cat760mmHg
• Flash Point: 100.2°C
• Appearance: /
• Density: 0.943g/cm³
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: tert-Butyl(4-methylphenyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl(4-methylphenyl) ketone(30314-44-4)
• EPA Substance Registry System: tert-Butyl(4-methylphenyl) ketone(30314-44-4)

Safety Data

• Hazardous Substances Data: 30314-44-4(Hazardous Substances Data)

Usage

General Description

Tert-butyl(4-methylphenyl) ketone, also known as 4-methyl-2,2-diphenylbutan-3-one, is a chemical compound with the molecular formula C15H20O. It is a white, crystalline solid with a faint, fruity odor. This chemical is primarily used as a flavoring agent and fragrance ingredient in various products, such as perfumes, soaps, and cosmetics. Tert-butyl(4-methylphenyl) ketone also possesses antioxidant properties and is used in the production of rubber and plastics as a stabilizer. Additionally, it has been found to have potential applications in the pharmaceutical industry for its anti-inflammatory and analgesic properties. However, it is important to handle this chemical with caution as it can be harmful if ingested, inhaled, or in contact with the skin.

InChI:InChI=1/C12H16O/c1-9-5-7-10(8-6-9)11(13)12(2,3)4/h5-8H,1-4H3

Upstream product

• 677-22-5 tert-butylmagnesium chloride 
• 104-85-8 para-methylbenzonitrile 
• 122-00-9 para-methylacetophenone 
• 74-88-4 methyl iodide 
• 630-18-2 tert-butyl isocyanide 
• 106-38-7 para-bromotoluene 
• 3282-30-2 pivaloyl chloride 
• 108-88-3 toluene 
• 95-46-5 2-methylphenyl bromide 
• 41394-66-5 potassium 3,3-dimethyl-2-oxobutyrate 
• 29540-83-8 p-tolyl triflate 
• 874-60-2 4-methyl-benzoyl chloride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 29097-50-5 t-butyl(p-tolyl)methyleneamine 

Downstream Products

• 31006-83-4 3-Hydroxy-4,4-dimethyl-3-p-tolyl-pentanoic acid ethyl ester 
• 6013-94-1 2,2-dimethyl-1-(4-methylphenyl)propan-1-ol 
• 123101-46-2 tert-Butyl (2RS,3RS)-3-hydroxy-2,4,4-trimethyl-3-p-tolylpentanoate 
• 123101-47-3 tert-Butyl (2RS,3SR)-3-hydroxy-2,4,4-trimethyl-3-p-tolylpentanoate 
• 52449-32-8 1-[4-(bromomethyl)phenyl]-2,2-dimethyl-1-propanone 
• 32018-31-8 4-pivaloyl-benzoic acid 
• 91456-99-4 2-(1,1-dimethylethyl)-2-(4-methylphenyl)-1,3-dioxolane 
• 50482-95-6 p-methylthiopivalophenone 
• 300539-07-5 cis-3,5-di-tert-Butyl-3,5-di-p-tolyl-1,2,4-trithiolane 

Relevant articles and documents

Synthesis of 1,2,4-Trithiolanes from Thione S-Oxides and Lawesson Reagent at Room Temperature

The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-oxide with Lawesson reagent (L. R.) afforded the corresponding 1,2,4-trithiolane. Thiopivalophenone and thiopivalophenone S-oxides reacted with L. R. at rt to give the corresponding S-sulfide, which further reacted with thiones to afford the corresponding cis-1,2,4-trithiolanes.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry

An efficient method for the synthesis of ketones using organolithium and acid chlorides under continuous flow conditions has been developed. In contrast to standard batch chemistry, over-addition of the organolithium to the ketone for the formation of the undesired tertiary alcohol has been minimised representing a direct approach toward ketones.