27644-00-4

Basic information

• Product Name: 2-(biphenyl-4-yl)-1-phenylethanone
• Synonyms: Biphenyl-4-acetophenone
• CAS NO: 27644-00-4
• Molecular Formula: C₂₀H₁₆O
• Molecular Weight: 272.3404
• Mol File: 27644-00-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 437.7°C at 760 mmHg
• Flash Point: 192.3°C
• Density: 1.102g/cm³
• Vapor Pressure: 7.3E-08mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 2-(biphenyl-4-yl)-1-phenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(biphenyl-4-yl)-1-phenylethanone(27644-00-4)
• EPA Substance Registry System: 2-(biphenyl-4-yl)-1-phenylethanone(27644-00-4)

Safety Data

• Hazardous Substances Data: 27644-00-4(Hazardous Substances Data)

Usage

Chemical Class

Aromatic ketones

Derivation

Derived from biphenyl and ethanone

Structure

Features a phenyl group attached to the second carbon atom of the ethanone backbone

Applications

a. Synthesis of pharmaceuticals (anti-inflammatory and analgesic drugs)
b. Production of fragrances and flavorings
c. Versatile intermediate in organic chemistry

Reactivity

Unique structure and reactivity make it a valuable component in the development of new chemical products and applications

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 644-08-6 4-Methylbiphenyl 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 98-86-2 acetophenone 
• 1591-31-7 4-iodo-biphenyl 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 1276111-26-2 [1,1′-biphenyl]-4-yl(mesityl)iodonium trifluoromethanesulfonate 
• 20383-28-2 N,N-diisopropyl benzamide 
• 31603-77-7 4-biphenylacetonitrile 
• 100-59-4 phenylmagnesium chloride 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 100-58-3 phenylmagnesium bromide 
• 264915-98-2 2-([1,1'-biphenyl]-4-yl)-N-methoxy-N-methylacetamide 
• 92-66-0 4-bromo-1,1'-biphenyl 

Downstream Products

• 36803-53-9 1-([1,1′-biphenyl]-4-yl)-2-phenylethane-1,2-dione 
• 112553-57-8 2-phenyl-9,10-phenanthrenequinone 
• 1283117-21-4 5-(biphenyl-4-yl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1416727-92-8 N-(2-(biphenyl-4-yl)-1-phenylethylidene)-4-methoxyaniline 
• 1416727-71-3 N-(2-(biphenyl-4-yl)-1-phenylethyl)-4-methoxyaniline 
• 149365-94-6 (2-Biphenyl-4-yl-1-phenyl-ethyl)-(2,2-diethoxy-ethyl)-amine 
• 149365-92-4 2-Biphenyl-4-yl-1-phenyl-ethylamine 
• 302777-51-1 2-(4'-biphenylyl)-1-phenylpropanone hydrazone 
• 302777-49-7 2-([1,1′-biphenyl]-4-yl)-1-phenylpropan-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.

Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation

The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].

The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers

tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.