27356-33-8

Basic information

• Product Name: 2-(2-METHOXYPHENYL)ACETOPHENONE
• Synonyms: 2-(2-METHOXYPHENYL)ACETOPHENONE;UKRORGSYN-BB BBV-5118605
• CAS NO: 27356-33-8
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• Mol File: 27356-33-8.mol
• Article Data: 19

Chemical Properties

• Melting Point: 104 °C
• Boiling Point: 350.849°C at 760 mmHg
• Flash Point: 153.709°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 2-(2-METHOXYPHENYL)ACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHOXYPHENYL)ACETOPHENONE(27356-33-8)
• EPA Substance Registry System: 2-(2-METHOXYPHENYL)ACETOPHENONE(27356-33-8)

Safety Data

• Hazardous Substances Data: 27356-33-8(Hazardous Substances Data)

Usage

Appearance

White to off-white solid.

Primary use

Intermediate in the production of other organic compounds.

Chemical structure

Benzene ring with a methoxy group and an acetyl group attached.

Classification

Ketone.

Fragrance

Sweet, floral scent.

Application in perfumes

Used as a fragrance ingredient in perfumes and other personal care products.

Pharmaceutical synthesis

Used in the synthesis of pharmaceuticals.

Dyes and pigments

Acts as a precursor in the production of various dyes and pigments.

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

Upstream product

• 1188264-46-1 N-methoxy-2-(2-methoxyphenyl)-N-methylacetamide 
• 100-58-3 phenylmagnesium bromide 
• 93-25-4 2-methoxyphenylacetic acid 
• 93-58-3 benzoic acid methyl ester 
• 578-58-5 2-methylmethoxybenzene 
• 100-66-3 methoxybenzene 
• 98-86-2 acetophenone 
• 20383-28-2 N,N-diisopropyl benzamide 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 34082-43-4 2-methoxybenzil 
• 55913-05-8 2-hydroxy-1-(2-methoxyphenyl)-2-phenylethan-1-one 
• 854630-15-2 2-(2-methoxyphenyl)-3-oxo-3-phenylpropanal 
• 68235-45-0 2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one 
• 578-57-4 2-bromoanisole 

Downstream Products

• 1839-72-1 2-phenylbenzofuran 
• 34082-43-4 2-methoxybenzil 
• 37883-67-3 5-(2-methoxyphenyl)-4-phenylpyrimidin-2-amine 
• 1309875-54-4 4-(2-methoxy-phenyl)-3-phenyl-cyclohex-2-enone oxime 
• 1309875-55-5 5-(2-methoxy-phenyl)-4-phenyl-1,5,6,7-tetrahydro-azepin-2-one 
• 1309875-53-3 4-(2-methoxy-phenyl)-3-phenyl-cyclohex-2-enone 
• 119824-87-2 1,3-diphenyl-4-orthomethoxyphenyl pyrazoline 
• 71490-84-1 1,3-diphenyl-4-orthomethoxyphenyl pyrazole 
• 119824-86-1 3-Dimethylamino-2-(2-methoxy-phenyl)-1-phenyl-propan-1-one 

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.

Electrochemical α-Arylation of Ketones via Anodic Oxidation of in Situ Generated Silyl Enol Ethers

An electrochemical procedure for the α-arylation of ketones has been developed. The method is based on the generation and one-pot anodic oxidation of silyl enol ethers in the presence of the arene. This strategy avoids isolation of the silyl enol intermediate and the utilization of external supporting electrolytes. Intermolecular arylations, which had not been reported so far, are possible when electron-rich arenes are utilized as coupling partners. The method has been demonstrated for a wide variety of aryl ketones and activated arenes, with moderate to good yields (up to 69%) obtained. Mechanistic insights and a theoretical rationale that explains the ketone α-arylation versus dimerization selectivity are also presented.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.