1120341-47-0

Basic information

• Product Name: (5-fluoropentyl)benzene
• Synonyms: (5-fluoropentyl)benzene
• CAS NO: 1120341-47-0
• Molecular Weight: 166.239
• Mol File: 1120341-47-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (5-fluoropentyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (5-fluoropentyl)benzene(1120341-47-0)
• EPA Substance Registry System: (5-fluoropentyl)benzene(1120341-47-0)

Safety Data

• Hazardous Substances Data: 1120341-47-0(Hazardous Substances Data)

Upstream product

• 1616365-94-6 (5-bromo-5-fluoropentyl)benzene 
• 768-56-9 4-Phenylbut-1-ene 
• 373-52-4 bromofluoromethane 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 112775-09-4 4-phenylbutyl 4-methylbenzenesulfonate 
• 10521-91-2 5-phenylpentan-1-ol 

Relevant articles and documents

Diversity-Oriented Synthesis of Aliphatic Fluorides via Reductive C(sp3)?C(sp3) Cross-Coupling Fluoroalkylation

Monofluorinated alkyl compounds are of great importance in pharmaceuticals, agrochemicals and materials. Herein, we describe a direct nickel-catalyzed monofluoromethylation of unactivated alkyl halides using a low-cost industrial raw material, bromofluoromethane, by demonstrating a general and efficient reductive cross-coupling of two alkyl halides. Results with 1-bromo-1-fluoroalkane also demonstrate the viability of monofluoroalkylation, which further established the first example of reductive C(sp3)-C(sp3) cross-coupling fluoroalkylation. These transformations demonstrate high efficiency, mild conditions, and excellent functional-group compatibility, especially for a range of pharmaceuticals and biologically active compounds. Mechanistic studies support a radical pathway. Kinetic studies reveal that the reaction is first-order dependent on catalyst and alkyl bromide whereas the generation of monofluoroalkyl radical is not involved in the rate-determining step. This strategy provides a general and efficient method for the synthesis of aliphatic fluorides.

Photoredox-Catalyzed Addition of Dibromofluoromethane to Alkenes: Direct Synthesis of 1-Bromo-1-fluoroalkanes

Reported herein is a direct and efficient route to 1-bromo-1-fluoroalkanes through the reaction of unactivated alkenes with dibromofluoromethane under photoredox catalysis. The key to the success of these addition reactions is the employment of a suitable photoredox catalyst. In particular, hydro- and bromo-bromofluoromethylated products were chemoselectively formed using THF and DMF/H2O as solvents, respectively. Furthermore, the synthetic application of the prepared 1-bromo-1-fluoroalkanes has been demonstrated by their transformation into a variety of fluorine-containing compounds.

Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.