22996-47-0

Basic information

• Product Name: 2,5-DIMETHYL-4'-METHOXYBENZOPHENONE
• Synonyms: 2,5-DIMETHYL-4'-METHOXYBENZOPHENONE;OTAVA-BB 1044047
• CAS NO: 22996-47-0
• Molecular Formula: C₁₆H₁₆O₂
• Molecular Weight: 240.3
• Mol File: 22996-47-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 88°C
• Boiling Point: 363.604°C at 760 mmHg
• Flash Point: 156.259°C
• Appearance: /
• Density: 1.072g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 2,5-DIMETHYL-4'-METHOXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYL-4'-METHOXYBENZOPHENONE(22996-47-0)
• EPA Substance Registry System: 2,5-DIMETHYL-4'-METHOXYBENZOPHENONE(22996-47-0)

Safety Data

• Hazardous Substances Data: 22996-47-0(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of p-anisoyl chloride with p-xylene,in the presence of aluminium chloride in methylene chloride between 10° and 20° (83%)in the presence of MoO2Cl2(20 mol%) at reflux for 20 h (31%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 65, p. 254, 2000 DOI: 10.1021/jo991055q

InChI:InChI=1/C16H16O2/c1-11-4-5-12(2)15(10-11)16(17)13-6-8-14(18-3)9-7-13/h4-10H,1-3H3

Upstream product

• 106-42-3 para-xylene 
• 833-79-4 t-butyl 4-methoxybenzoate 
• 201230-82-2 carbon monoxide 
• 100-66-3 methoxybenzene 
• 100-07-2 4-methoxy-benzoyl chloride 
• 22328-43-4 2,5-dimethylbenzoyl chloride 
• 794-94-5 p-Methoxybenzoic anhydride 
• 77775-86-1 4-Methoxybenzoesaeure-difluorophosphorsaeure-anhydrid 
• 100-09-4 4-methoxybenzoic acid 
• 696-62-8 para-iodoanisole 

Downstream Products

• 89651-85-4 3-bromo-4-methoxy-2',5'-dimethyldiphenylmethane 
• 89651-84-3 3-bromo-4-hydroxy-2',5'-dimethylphenylmethane 
• 618120-27-7 [(4-methoxyphenyl)methyl]terephthalic acid 
• 618120-26-6 (4-methoxybenzoyl)terephthalic acid 
• 89651-83-2 3-bromo-4-methoxy-2',5'-dimethylbenzophenone 
• 22996-48-1 1--1-<2'.5'-xylenyl>-ethanol 

Relevant articles and documents

A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide

We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.

A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation

The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.

MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation

The use of MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation is described. A series of aromatic ketones and sulfones were prepared in moderate to good yields using acyl chloride or sulfonyl chloride in the presence of MoO2Cl2 (20 mol %), under solvent-free conditions.