458-87-7

Basic information

• Product Name: (2-fluoroethyl)benzene
• CAS NO: 458-87-7
• Molecular Formula: C₈H₉F
• Molecular Weight: 124.1555
• Mol File: 458-87-7.mol

Chemical Properties

• Boiling Point: 156.3°C at 760 mmHg
• Flash Point: 38°C
• Density: 0.972g/cm³
• Vapor Pressure: 3.74mmHg at 25°C
• Refractive Index: 1.475
• CAS DataBase Reference: (2-fluoroethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2-fluoroethyl)benzene(458-87-7)
• EPA Substance Registry System: (2-fluoroethyl)benzene(458-87-7)

Safety Data

• Hazardous Substances Data: 458-87-7(Hazardous Substances Data)

Upstream product

• 105983-86-6 phenethylnaphthalene-2-sulfonate 
• 151588-78-2 (2-bromo-2-fluoroethyl)benzene 
• 54448-36-1 [2-(trifluoromethylsulfonyloxy)ethyl]benzene 
• 122-78-1 phenylacetaldehyde 
• 60-12-8 2-phenylethanol 
• 17376-04-4 2-phenethyl iodide 
• 4455-09-8 2-phenylethyl tosylate 
• 501-52-0 3-Phenylpropionic acid 
• 116113-96-3 2,4,6-Trimethyl-benzenesulfonic acid phenethyl ester 
• 103-63-9 1-phenyl-2-bromoethane 
• 114263-63-7 C₁₄H₁₃FS 
• 622-24-2 2-phenylethyl chloride 
• 20020-27-3 2-phenylethyl mesylate 

Downstream Products

• 1064664-64-7 1-methyl-4-(4-phenylbut-1-yn-1-yl)benzene 
• 42524-30-1 (3-methylpent-4-en-1-yl)benzene 
• 103-63-9 1-phenyl-2-bromoethane 
• 622-24-2 2-phenylethyl chloride 
• 17376-04-4 2-phenethyl iodide 
• 56153-06-1 1-(2-fluoroethyl)-4-nitrobenzene 
• 113399-22-7 1-(1-Chloro-2-fluoro-ethyl)-4-fluoro-benzene 
• 325-55-3 1-fluoro-2-chloro-2-phenylethane 
• 55153-06-5 2-bromo-1-fluoro-2-phenylethane 
• 100-42-5 styrene 
• 538-86-3 benzyl methyl ether 
• 3558-60-9 1-methoxy-2-phenylethane 
• 4013-34-7 3-phenyl-2-oxabutane 
• 100-52-7 benzaldehyde 

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.

A Series of Deoxyfluorination Reagents Featuring OCF2Functional Groups

Research on perfluoroalkyl ether carboxylic acids (PFECAs) as alternatives for perfluoroalkyl substances continues with the goal of protecting the environment. However, very little is known about the utilization of decomposition products of PFECAs. We report herein a new series of deoxyfluorination reagents featuring OCF2 functional groups derived from certain PFECAs. Alkyl fluorides were generated from various alcohols in ≤97% yield by these novel reagents. The mechanistic experiment verified in situ generation of carbonic difluoride (COF2).

Copper-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents

Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product. Making the switch: A copper-hydride species, generated by the treatment of a copper salt with alkyl Grignard reagents, catalyzes the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides and Grignard reagents. The alkyl group of the alkyl fluoride is selectively introduced to an internal carbon atom of the 1,3-diene and the Grignard reagent acts as hydride source to give the branched terminal alkene, even in the presence of alkenes and alkynes.

Mild copper-catalyzed fluorination of alkyl triflates with potassium fluoride

A chemoselective catalytic fluorination of alkyl triflates is described using potassium fluoride as a fluoride source. Excellent yields of the desired alkyl fluorides are obtained after one hour at 45°C using 2 mol% of the copper catalyst. With 10 mol% of the catalyst, full conversion can be achieved in less than 10 minutes at 45°C, and thus makes this procedure potentially suited for the preparation of 18F-labeled PET probes. As a result of the mild reaction conditions, only the substitution products are observed with no evidence of common side reactions, such as elimination. Reported is a preliminary study of the reaction scope, which demonstrates that the fluorination can be performed in the presence of a wide range of functional groups. Evidence suggests an unusual role of the [IPrCuOTf] catalyst as a phase-transfer catalyst and points to [IPrCuF] as the active fluorinating reagent (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).

Ionic liquids as recyclable solvents for diethylaminosulfur trifluoride (DAST) mediated fluorination of alcohols and carbonyl compounds

The first simple and efficient method for the synthesis of mono and gem-difluorinated molecules using [C8mim][PF6] ionic liquid as a recyclable solvent medium with diethylaminosulfur trifluoride (DAST) as the fluorinating reagent, is reported.

1,1,3,3,3-Pentafluoropropene secondary amine adducts new selective fluorinating agents

Addition of secondary amine SA (dimethylamine DMA, diethylamine DEA, pyrrolidine Pyr, piperidine Pip, morpholine Mor) to pentafluoropropene PFP gives rise to generation of mixtures of two products (1-dialkylamine-1,3,3,3-tetrafluoropropene and N,N-dialkyl-1,1,3,3,3-pentafluoropropylamine) in different ratios. Those reaction mixtures, however, were found to be efficient fluorinating agents replacing hydroxyl groups in alcohols into fluorine. In general, they react with alcohols yielding corresponding fluorides, equimolar amounts of appropriate 3,3,3-trifluoropropionamide and hydrogen fluoride. Aliphatic primary alcohols including octanol and benzylic alcohol yield only alkyl fluorides. The secondary and tertiary alcohols, beside the desired fluorides, give usually considerably amount of alkenes.

A novel fluorinated erythromycin antibiotic

A novel fluorinated erythromycin (16-fluoroerythromycin A) has been produced by Saccharopolyspora erythraea ERMD1, using precursor-directed biosynthesis. The Royal Society of Chemistry 2005.

1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent

The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.

Fluorination with aminosulfur trifluorides

A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.

Fluorination with aminosulfur trifluorides

A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.