71298-03-8

Usage

Physical state at room temperature

Yellow crystalline solid

Primary uses

a. Production of pharmaceuticals
b. Production of perfumes

Additional use

Building block in the synthesis of other organic compounds

Chemical classification

Ketone

Odor

Strong, sweet, and floral

Safety precautions

a. Harmful if ingested or inhaled
b. Can cause skin and eye irritation upon contact
c. Potential to cause respiratory sensitization
d. Proper handling and safety measures required when working with the compound

Upstream product

• 100-44-7 benzyl chloride 
• 93-91-4 1-phenylbutan-1,3-dione 
• 613-90-1 benzoyl cyanide 
• 97394-41-7 S-(4-nitrophenyl) 3-phenylpropanethioate 
• 31729-70-1 bis(iodozinc)methane 
• 100-39-0 benzyl bromide 
• 2550-26-7 4-Phenyl-2-butanone 
• 98-88-4 benzoyl chloride 
• 61157-35-5 2-chloro-3-phenylpropionyltrimethylsilane 
• 98-86-2 acetophenone 
• 103-25-3 3-phenylpropanoic acid methyl ester 

Downstream Products

• 94223-00-4 4-methyl-3-phenyl-5-phenethyl-1H-pyrazole 
• 94223-10-6 1,5-diphenyl-2-methylpenta-1,3-dione 
• 113060-95-0 3-phenethyl-5-phenyl-1⁽²⁾H-pyrazole 
• 65-85-0 benzoic acid 
• 501-52-0 3-Phenylpropionic acid 

Relevant academic research and scientific papers

Chemo- and regioselective preparation of zinc enolate from thiol esters by palladium catalyzed cross-coupling reaction

The palladium catalyzed cross-coupling reaction of thiol esters with bis(iodozincio)methane or 1,1-bis(iodozincio)ethane gave Reformatsky-type enolates. They can react with some electrophiles to give the corresponding adducts and were also trapped by silylation reagents to afford silyl enol ethers. As the method applicable to the thiol ester carrying ketone moiety, it afforded zinc enolates carrying ketone in the same molecule.

Chemo- and regioselective preparation and reaction of a kinetic zinc enolate formed from a thiol ester and bis(iodozincio)methane

(Chemical Equation Presented) Reactive functionalized enolates that are otherwise difficult to obtain can be prepared in a simple procedure by the treatment of a thiol ester with bis(iodozincio)methane in the presence of a palladium catalyst (see scheme). The terminal zinc enolates thus formed are kinetically controlled and react with a variety of electrophiles, such as aldehydes, ketones, and acyl cyanides. FG = functional group.

Mild conversion of β-diketones and β-ketoesters to carboxylic acids

A mild protocol for the conversion of β-ketoesters and β-diketones to carboxylic acids with use of CAN in CH3CN is described. The method is compatible with a number of functional groups, and can generate carboxylic acids under neutral conditions at room temperature. The reaction is fast and general, providing an alternative method to the commonly used malonic ester acid preparation. Initial mechanistic studies show that initial oxidation of the enol form of the β-dicarbonyl initiates the reaction. The presence of nitrate as an oxidant ligand or as an additive is critical for success of the reaction.