329-77-1

Usage

Chemical structure

1-(4-chlorophenyl)-2-fluoroethanol is a chemical compound with a 2-fluoroethanol molecule and a 4-chlorophenyl group attached to the first carbon atom.

Physical state

It is a colorless liquid.

Molecular weight

The molecular weight of 1-(4-chlorophenyl)-2-fluoroethanol is 166.6 g/mol.

Safety measures

It is important to handle 1-(4-chlorophenyl)-2-fluoroethanol with proper safety measures, as it can be harmful if swallowed, inhaled, or in contact with skin.

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 98506-75-3 2-Benzenesulfonyl-1-(4-chloro-phenyl)-2-fluoro-ethanol 
• 104-88-1 4-chlorobenzaldehyde 
• 108-90-7 chlorobenzene 
• 373-53-5 fluoroiodomethane 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 329-78-2 1-(4-chlorophenyl)-2-fluoroethan-1-one 

Relevant academic research and scientific papers

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy

The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

Synthesis of enantiopure fluorohydrins using alcohol dehydrogenases at high substrate concentrations

The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.

Palladium-catalyzed intermolecular fluoroesterification of styrenes: Exploration and mechanistic insight

A novel palladium-catalyzed intermolecular oxidative fluoroesterification of vinylarenes has been developed using NFSI, one of the mildest electrophilic fluorinating reagents. The reaction presents an efficient synthetic pathway to afford a series of α-monofluoromethylbenzyl carboxylates in good to excellent yields. Rather than following an electrophilic fluorination pathway, the reaction is initiated through oxidation of Pd(0) to a Pd(ii) fluoride complex by NFSI, followed by fluoropalladation of a styrene to generate an α-monofluoromethylbenzyl-Pd intermediate. Generally, reductive elimination of benzyl-PdII complexes is favored with relatively strong oxy-nucleophiles to afford C-O bonds. This reaction, however, exhibited the opposite reactivity: strong acids with weak nucleophilicity, such as CF 3CO2H and CCl3CO2H, were prone to afford the fluoroesterification product, while weak acids with strong nucleophilicity, such as HOAc and BzOH, did not deliver the C-O bond product. Further mechanistic studies determined that Csp3-Pd(O2CR), a key intermediate, was generated through ionic ligand exchange between benzyl-Pd(NZ2) and CF3CO2H, and the final C-O bond was possibly formed through reductive elimination of a high-valent Csp 3-Pd(O2CR) complex via an SN2-type nucleophilic attack pathway.

Facile preparation of difluoromethyl- and monofluoromethyl-containing amides via Ritter reaction

Both secondary and tertiary difluoromethylated carbinols were found to readily react with acetonitrile under the catalysis of concentrated sulfuric acid to give the corresponding difluoromethylated acetamides in good yields, which is remarkably more effic

Effect of reaction conditions on the kinetic and activation parameters for the mild introduction of fluorine into α-substituted styrenes with AccufluorTM NFTh

Kinetic studies on fluorination of α-substituted styrenes with 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (AccufluorTM NFTh) in acetonitrile or in acetonitrile in the presence of methanol or water as nucleophiles were carried out. These reactions exhibited overall second-order kinetics and formed Markovnikov type products. The corresponding second-order rate constants for fluorination of the studied substrates in the presence of methanol at 38.8 deg C are k2 = 1.1 x 10-3 M-1 s-1 for styrene (1a), 3.3 x 10-2 M-1 s-1 for α-methylstyrene (1b) and 3.4 x 10-2 M-1 s-1 for 1,1-diphenylethene (1c). The substitution of methanol as nucleophile by water had very little effect on the rate of the process. Solvent polarity variation (Grunwald-Winstein Ybenzyl) showed a similar small effect, too, indicating negligible change in the polarity of the rate-determining transition state in comparison with the reactants. Activation enthalpies (between 62 and 80 kJ mol-1) and activation antropies (between -74 and 32 J mol-1 K-1) were determined for fluorination of α-substituted styrenes with NFTh in acetonitrile in the presence of methanol and water as nucleophiles. Hammett correlation analysis of the reaction of substituted styrenes with NFTh in MeCN MeCN-H2O and MeCN-MeOH gave reaction constants ρ+ of -1.48, -1.52 and -1.80, respectively, which support our belief in the mainly non-polar character of the rate-determining transition state of the studied reactions.