863506-06-3

Basic information

• Product Name: 4-fluoro-4-phenylbutan-2-one
• Synonyms: 4-fluoro-4-phenylbutan-2-one
• CAS NO: 863506-06-3
• Molecular Weight: 166.195
• Mol File: 863506-06-3.mol

Chemical Properties

• CAS DataBase Reference: 4-fluoro-4-phenylbutan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluoro-4-phenylbutan-2-one(863506-06-3)
• EPA Substance Registry System: 4-fluoro-4-phenylbutan-2-one(863506-06-3)

Safety Data

• Hazardous Substances Data: 863506-06-3(Hazardous Substances Data)

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 19961-42-3 (E)-1-methyl-2-phenyl-1-cyclopropanol 
• 17488-65-2 4-phenylbut-3-en-2-ol 

Relevant articles and documents

Iodine(III)-mediated fluorination/semipinacol rearrangement cascade of 2-alkylidenecyclobutanol derivatives: Access to β-monofluorinated cyclopropanecarbaldehydes

A hypervalent iodine(III)-mediated ring-contractive fluorination reaction of 2-alkylidenecyclobutanol derivatives is presented. The protocol allows the facile synthesis of βmonofluorinated cyclopropanecarbaldehydes via a fluorination/ semipinacol rearrangement cascade using nucleophilic Py·HF as the fluorine source. For challenging electron-rich arene substrates, the installation of a protecting group on the free alcohol is pivotal for maintaining the reaction efficiency. The synthetic utility was demonstrated by the scalability of this reaction and further transformations of the products.

Site-selective approach to β-fluorination: Photocatalyzed ring opening of cyclopropanols

To expand upon the recent pioneering reports of catalyzed sp3 C-H fluorination methods, the next rational step is to focus on directing "radical-based fluorination" more effectively. One potential solution entails selective C-C bond activation

AgII-Mediated Synthesis of β-Fluoroketones by Oxidative Cyclopropanol Opening

A regioselective synthesis of β-fluorinated ketones by silver(II)-mediated ring opening is described. Commercially available AgF2 serves as both an oxidant and fluorine-atom source. A variety of β-fluorinated ketones are efficiently prepared from tertiary cyclopropanol precursors, offering a straightforward approach for the introduction of a fluorine atom at a remote site. Selectivity is observed in the site of bond cleavage, which leads to fluorination at the more substituted site. A radical mediated sequential homolytic C–C bond cleavage and C–F bond formation is suggested.

Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones

The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.

Triethylborane-initiated radical chain fluorination: A synthetic method derived from mechanistic insight

We offer a mild, metal-free sp3 C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane.an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.

Iron(II)-catalyzed benzylic fluorination

Direct C-F functionalization of benzylic sp3 C-H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to β-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to α,β-unsaturated ketones.

Visible light-promoted metal-free C-H activation: Diarylketone-catalyzed selective benzylic mono- and difluorination

We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.