42916-68-7

Usage

Compound class

Ketone

Physical state

Colorless liquid

Odor

Sweet, floral

Uses

Flavor and fragrance agent in food and cosmetics, intermediate in pharmaceutical synthesis, production of pesticides, potential use in polymer and other industrial chemical processes

Safety precautions

May be harmful if ingested or inhaled, can cause skin and eye irritation, handle with caution.

Upstream product

• 109-72-8 n-butyllithium 
• 226260-01-1 3-fluoro-N-methoxy-N-methylbenzamide 
• 684648-38-2 2-(3-fluoro-phenyl)-[1,3,2]dioxaborinane 
• 120-92-3 cyclopentanone 
• 1598-19-2 1-(3-fluorophenyl)-pentan-1-ol 
• 403-54-3 m-Fluorobenzonitrile 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.

A Rapid Injection NMR Study of the Reaction of Organolithium Reagents with Esters, Amides, and Ketones

Unexpectedly high rates of reaction between alkyllithium reagents and amides, compared to esters and ketones, were observed by Rapid Inject NMR and competition experiments. Spectroscopic investigations with 4-fluorophenyllithium (ArLi, mixture of monomer and dimer in THF) and a benzoate ester identified two reactive intermediates, a homodimer of the tetrahedral intermediate, stable below -100°C, and a mixed dimer with ArLi. Direct formation of dimers suggested that the ArLi dimer may be the reactive aggregate rather than the usually more reactive monomer. In contrast, RINMR experiments with ketones demonstrated that the ArLi monomer was the reactive species. (Chemical Equation Presented).

Axially chiral NHC-Pd(II) complexes in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant

(Chemical Equation Presented) Axially chiral N-heterocyclic carbene (NHC) Pd(II) complexes were prepared from optically active 1,1′-binaphthalenyl- 2,2′-diamine (BINAM) and H8-BINAM and applied in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant. The corresponding sec-alcohols can be obtained in good yields with moderate to good enantioselectivities.

Facile Synthesis of 2-Bromo-3-fluorobenzonitrile: An Application and Study of the Halodeboronation of Aryl Boronic Acids

A scaleable synthesis of 2-bromo-3-fluorobenzonitrile via the NaOMe-catalyzed bromodeboronation of 2-cyano-6-fluorophenylboronic acid was developed. The generality of this transformation was demonstrated through the halodeboronation of a series of aryl boronic acids. Both aryl bromides and aryl chlorides were formed in good to excellent yields when the corresponding aryl boronic acid was treated with 1,3-dihalo-5,5-dimethylhydantoin and 5 mol % NaOMe.