33470-10-9

Basic information

• Product Name: 2'-METHOXY-2-PHENYLACETOPHENONE
• Synonyms: 2'-METHOXY-2-PHENYLACETOPHENONE
• CAS NO: 33470-10-9
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• Mol File: 33470-10-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 357.3°C at 760 mmHg
• Flash Point: 158.1°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 2.76E-05mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2'-METHOXY-2-PHENYLACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-METHOXY-2-PHENYLACETOPHENONE(33470-10-9)
• EPA Substance Registry System: 2'-METHOXY-2-PHENYLACETOPHENONE(33470-10-9)

Safety Data

• Hazardous Substances Data: 33470-10-9(Hazardous Substances Data)

Usage

Preparation

Obtained by deamination of 2-amino-1-(2-methoxyphenyl)-1-phenyletha-nol with sodium nitrite in 50% aqueous acetic acid at 0° Also obtained by reaction of 2-methoxybenzamide with benzylmagnesium bromide.

InChI:InChI=1/C15H14O2/c1-17-15-10-6-5-9-13(15)14(16)11-12-7-3-2-4-8-12/h2-10H,11H2,1H3

Upstream product

• 146767-33-1 phenylazo tert-butyl sulfide 
• 34589-94-1 2-amino-1-(2-methoxy-phenyl)-1-phenyl-ethanol 
• 64-19-7 acetic acid 
• 529-28-2 4-iodoanisol 
• 103-80-0 phenylacetyl chloride 
• 31949-21-0 bromomethyl 2-methoxyphenyl ketone 
• 1619239-39-2 1-(2-(2-methoxyphenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate 
• 72867-68-6 N-[1-Cyano-1-(2-methoxy-phenyl)-2-phenyl-ethyl]-N-phenyl-benzamide 
• 64139-02-2 3-(2-methoxy-phenyl)-3-oxo-2-phenyl-propionitrile 
• 606-45-1 2-methoxybenzoic acid methyl ester 
• 108-88-3 toluene 
• 130250-62-3 2-methoxy-N-methoxy-N-methylbenzamide 
• 100-66-3 methoxybenzene 
• 21615-34-9 2-Methoxybenzoyl chloride 

Downstream Products

• 574-12-9 isoflavone 
• 34082-43-4 2-methoxybenzil 
• 1428476-53-2 (R)-2-(2-methoxyphenyl)-4-methyl-1-phenylpent-4-en-2-ol 
• 60312-67-6 2-phenyl-3(2H)-benzxofuranone 
• 250675-83-3 2-methoxy-α-phenyl-α-diazoacetophenone 
• 101435-17-0 2-methoxy-deoxybenzoin semicarbazone 
• 2491-31-8 2-hydroxy-deoxybenzoin 

Relevant articles and documents

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Synthesis of unsymmetrical ketones by applying visible-light benzophenone/nickel dual catalysis for direct benzylic acylation

Herein, we report a dual catalytic system for the direct benzylic C-H acylation reaction furnishing a variety of unsymmetrical ketones. A benzophenone-derived photosensitizer combined with a nickel catalyst has been established as the catalytic system. Both acid chlorides and anhydrides are able to acylate the benzylic position of toluene and other methylbenzenes. The method offers a valuable alternative to late transition metal catalyzed C-H acylation reactions.

Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones

A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.