24155-34-8

Basic information

• Product Name: 2-(1H-imidazol-1-yl)-1-phenylethanone
• Synonyms: 2-(1-Imidazolyl)acetophenone; 5-23-04-00371 (Beilstein Handbook Reference); Acetophenone, 2-(imidazol-1-yl)-; ethanone, 2-(1H-imidazol-1-yl)-1-phenyl-; Ethanone, 2-(1H-imidazol-1-yl)-1-phenyl- (9CI)
• CAS NO: 24155-34-8
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.2099
• Mol File: 24155-34-8.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 395°C at 760 mmHg
• Flash Point: 192.7°C
• Density: 1.12g/cm³
• Vapor Pressure: 1.9E-06mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 2-(1H-imidazol-1-yl)-1-phenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-imidazol-1-yl)-1-phenylethanone(24155-34-8)
• EPA Substance Registry System: 2-(1H-imidazol-1-yl)-1-phenylethanone(24155-34-8)

Safety Data

• Hazardous Substances Data: 24155-34-8(Hazardous Substances Data)

Usage

Class

Aryl-ketones

Appearance

White to yellow crystalline powder

Solubility

Soluble in organic solvents

Odor

Mild, characteristic

Uses

Building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Structure and properties

Versatile and useful intermediate in organic chemistry

Upstream product

• 288-32-4 1H-imidazole 
• 70-11-1 α-bromoacetophenone 
• 3282-32-4 2-diazo-acetophenone 
• 100-42-5 styrene 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 98-86-2 acetophenone 
• 2142-69-0 2-bromophenyl methyl ketone 

Downstream Products

• 24169-71-9 N-hydroxy-2-(1H-imidazol-1-yl)-1-phenylethanimine 
• 110232-83-2 2-(1H-imidazol-1-yl)-1,3-diphenylprop-2-en-1-one 
• 288-32-4 1H-imidazole 
• 1353720-26-9 2-(imidazol-1-yl)-1-phenylethanone* (5-nitrosalicylic acid) 
• 1058142-86-1 2-(imidazol-1-yl)-1-phenylethanone*(2,4,6-trinitrophenol) 
• 1353720-25-8 2-(imidazol-1-yl)-1-phenylethanone* (m-nitrobenzoic acid) 

Relevant articles and documents

An efficient catalytic asymmetric route to 1-aryl-2-imidazol-1-yl-ethanols

The asymmetric hydrogenation of 1-aryl-2-imidazol-1-yl-ethanones offers a concise route to homochiral 1-aryl-2-imidazol-1-yl-ethanols. Catalytic asymmetric transfer hydrogenation with formic acid using [(R,R)-TsDPEN] Ru(Cymene)Cl as precatalyst was shown to be effective in this transformation. Preliminary process development showed that the hydrogenation could be carried out under mild conditions at a molar substrate-to-catalyst (S/C) ratio of 1000-2000.

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

One pot synthesis of α-N-heteroaryl ketone derivatives from aryl ketones using aqueous NaICl2

A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.

α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species

Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.