53291-89-7

Basic information

• Product Name: 2,5-DIMETHYLPHENYLACETONE
• Synonyms: 2-TOLOYLACETONE;2,5-DIMETHYLPHENYLACETONE;2,5-Dimethylphenylacetone,99+%;1-(2,5-dimethylphenyl)propan-2-one
• CAS NO: 53291-89-7
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 53291-89-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 244.5°Cat760mmHg
• Flash Point: 104.7°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 0.0303mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: 2,5-DIMETHYLPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYLPHENYLACETONE(53291-89-7)
• EPA Substance Registry System: 2,5-DIMETHYLPHENYLACETONE(53291-89-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 53291-89-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

InChI:InChI=1/C11H14O/c1-8-4-5-9(2)11(6-8)7-10(3)12/h4-6H,7H2,1-3H3

Upstream product

• 26562-24-3 3-bromo-2-methoxypropene 
• 106-42-3 para-xylene 
• 84784-30-5 1-(2,5-Dimethyl-phenyl)-1-methylsulfanyl-propan-2-one 
• 94169-21-8 1-(2,5-Dimethyl-phenyl)-propan-2-one O-methyl-oxime 
• 2493-58-5 2,5-dimethylphenyl tosylate 
• 67-64-1 acetone 
• 553-94-6 4-bromo-m-xylene 

Relevant articles and documents

Palladium-Catalyzed Mono-α-arylation of Acetone at Room Temperature

The first examples of acetone mono-α-arylation at room temperature are described, enabled by use of a [Pd(cinnamyl)Cl]2/JosiPhos catalyst system. (Hetero)aryl chloride, bromide, and iodide electrophiles featuring or lacking ortho-substitution, and comprising a range of functionalities (e.g., alkoxy, cyano, fluoro, trifluoromethyl, or alkenyl) and heteroaryl motifs (e.g., pyrrole, pyridine, isoquinoline, quinoline, quinaldine, (benzo)thiophene, benzothiazole, or benzodioxole) were successfully accommodated. Proof-of-principle experiments confirm that other (hetero)aryl methyl ketones can also be employed in such room temperature mono-α-arylations. The established substrate scope is the most extensive reported to date for acetone mono-α-arylation under any conditions, and more generally represents the first room temperature ketone mono-α-arylations employing a structurally diverse set of (hetero)aryl chlorides. Chill out: The first examples of acetone mono-α-arylation at room temperature are described. The substrate scope is the most extensive reported to date for acetone mono-α-arylation under any conditions, and represents the first room temperature ketone mono-α-arylations employing a diverse set of (hetero)aryl chlorides.

Novel Electrophilic Species Equivalent to α-Keto Cations. Reactions of O,O-Diprotonated Nitro Olefins with Benzenes Yield Arylmethyl Ketones

The N,N-dihydroxyiminium carbenium ions formed by O,O-diprotonation of nitro olefins in a strong acid, trifluoromethanesulfonic acid (TFSA), are discrete and novel dipositively charged species.The dications formed from α-substitited nitroethylenes are reactive electrophiles to give α-arylated ketones in high yields.This constitutes a versatile synthetic method for the preparation of α-arylated ketones, which are difficult to synthesize by the conventional Friedel-Crafts reactions.

Syntheses of Arylacetone and Arylacetonitrile by Friedel-Crafts Reaction with α-Chloro-α-(methylthio)-substituted Acetone and Acetonitrile

Novel preparative methods for arylacetone and arylacetonitrile are described.Friedel-Crafts reactions of aromatic compounds with α-chloro-α-(methylthio)acetone (4) and α-chloro-α-(methylthio)acetonitrile (7) in the presence of Lewis acid afforded α-(methylthio)arylacetone (5) and α-(methylthio)arylacetonitrile (8), respectively.Compounds (5) and (8) were converted into the corresponding arylacetone (6) and arylacetonitrile (9) by reduction with zinc dust in acetic acid.Keywords: Friedel-Crafts reaction with α-chloro-α-(methylthio)acetone; Friedel-Crafts reaction with α-chloro-α-(methylthio)acetonitrile; α-(methylthio)arylacetone; α-(methylthio)arylacetonitrile; arylacetone; arylacetonitrile; reductive desulfurization; zinc dust-acetic acid