350-50-5

Usage

Uses

Used in Organic Synthesis:
Benzyl fluoride is used as a key intermediate in the synthesis of various organic compounds. Its reactivity and stability contribute to its widespread use in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, benzyl fluoride is utilized as a building block for the development of new drugs. Its unique structure allows for the creation of novel molecular entities with potential therapeutic applications.
Used in Agrochemical Industry:
Benzyl fluoride is also employed in the agrochemical sector for the synthesis of various pesticides and other crop protection agents. Its properties enable the development of effective and environmentally friendly solutions for agricultural use.
Used in Fluorination Reagents:
Benzyl fluoride serves as a precursor for the preparation of fluoro amino, fluoro enamino, and other fluorination reagents. These reagents are essential in the synthesis of fluorinated organic compounds, which have a wide range of applications, including the development of new materials with improved properties.
Used in Fluorochemicals Production:
Benzyl fluoride is used as a starting material for the production of various fluorochemicals, such as (fluoroalkyl)benzenes. These compounds are valuable in the synthesis of fluorinated polymers, which exhibit enhanced properties compared to their non-fluorinated counterparts.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 2250, 1974 DOI: 10.1021/ja00814a044Tetrahedron Letters, 28, p. 4733, 1987 DOI: 10.1016/S0040-4039(00)96612-7The Journal of Organic Chemistry, 48, p. 4158, 1983 DOI: 10.1021/jo00170a072

Hazard

Very irritant.

InChI:InChI=1/C8H7ClFNO/c9-5-8(12)11-7-3-1-2-6(10)4-7/h1-4H,5H2,(H,11,12)

Upstream product

• 908094-04-2 phenyldiazomethane 
• 103-82-2 phenylacetic acid 
• 122-78-1 phenylacetaldehyde 
• 100-39-0 benzyl bromide 
• 108-95-2 phenol 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 100-44-7 benzyl chloride 
• 71742-14-8 1-Benzyl-2,4,6-triphenyl-pyridinium; fluoride 
• 75864-90-3 N-benzyl-5,6-dihydro-2,4-diphenylbenzo quinolinium tetrafluoroborate 
• 100-51-6 benzyl alcohol 
• 56-23-5 tetrachloromethane 
• 108-88-3 toluene 
• 134613-19-7 3-benzyloxy-3-fluorodiazirine 
• 67-56-1 methanol 

Downstream Products

• 539-30-0 1-(ethoxymethyl)benzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 500-11-8 4-nitrobenzyl fluoride 
• 1520-42-9 1,1,2-triphenylethane 
• 101-81-5 Diphenylmethane 
• 834-14-0 p-benzylanizole 
• 883-90-9 o-benzyl anisole 
• 6852-58-0 N-benzylidene tert-butylamine 
• 3378-72-1 N-tert-butylbenzylamine 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 455-94-7 1-(fluoromethyl)-3-nitrobenzene 
• 100-51-6 benzyl alcohol 
• 4428-13-1 1,1,2-Triphenylethanol 
• 1944-01-0 1-benzylcyclohexan-1-ol 

Relevant academic research and scientific papers

C?F Bond Activation by Silylium Cation/Phosphine Frustrated Lewis Pairs: Mono-Hydrodefluorination of PhCF3, PhCF2H and Ph2CF2

Single defluorination of aryl polyfluoromethyl functionalities is achieved by both intra- and intermolecular silylium cation/phosphine Lewis pairs. Phosphine-captured aryl fluoromethyl cations are then treated with Br?nsted base to complete the first mono

A class of phase-transfer catalyst with interionic strain: Insight into the bonding of disubstituted N-vs carbene-stabilized NI-centered cations

The straightforward synthesis of a class of nitrogen-based phase-transfer catalysts (PTCs) having markedly dissociated anions due to interionic donor-donor "ion pair strain" and use for catalyzing benzylation and benzylic fluorination is reported. Provided also is insight into the bonding of disubstituted N- vs so-called divalent carbene-stablized NI-centered cations and the unprecedented finding of a cyclopropenium based C-H···πaryl interaction.

Catalytic Formation of C(sp3)-F Bonds via Heterogeneous Photocatalysis

Due to their chemical, physical, and biological properties, fluorinated compounds are widely employed throughout society. Yet, despite their critical importance, current methods of introducing fluorine into compounds suffer from severe drawbacks. For example, several methods are noncatalytic and employ stoichiometric equivalents of heavy metals. Existing catalytic methods, on the other hand, exhibit poor activity, generality, selectivity and/or have not been achieved by heterogeneous catalysis, despite the many advantages such an approach would provide. Here, we demonstrate how selective C(sp3)-F bond synthesis can be achieved via heterogeneous photocatalysis. Employing TiO2 as photocatalyst and Selectfluor as mild fluorine donor, effective decarboxylative fluorination of a variety of carboxylic acids can be achieved in very short reaction times. In addition to displaying the highest turnover frequencies of any reported fluorination catalyst to date (up to 1050 h-1), TiO2 also demonstrates excellent levels of durability, and the system is catalytic in the number of photons required; i.e., a photon efficiency greater than 1 is observed. These factors, coupled with the generality and mild nature of the reaction system, represent a breakthrough toward the sustainable synthesis of fluorinated compounds.

Fluorine as a hydrogen-bond acceptor: Experimental evidence and computational calculations

Hydrogen-bonding interactions play an important role in many chemical and biological systems. Fluorine acting as a hydrogen-bond acceptor in intermolecular and intramolecular interactions has been the subject of many controversial discussions and there are different opinions about it. Recently, we have proposed a correlation between the propensity of fluorine to be involved in hydrogen bonds and its 19F NMR chemical shift. We now provide additional experimental and computational evidence for this correlation. The strength of hydrogen-bond complexes involving the fluorine moieties CH 2F, CHF2, and CF3 was measured and characterized in simple systems by using established and novel NMR methods and compared to the known hydrogen-bond complex formed between acetophenone and p-fluorophenol. Implications of these results for 19F NMR screening are analyzed in detail. Computed values of the molecular electrostatic potential at the different fluorine atoms and the analysis of the electron density topology at bond critical points correlate well with the NMR results.

New fluoride ion reagent from pentafluoropyridine

A new nucleophilic fluorinating agent, derived from reaction of dimethylaminopyridine (DMAP) with pentafluoropyridine, has been synthesised and assessed in various carbon-fluorine bond forming processes.

Polymer-Supported Potassium Fluoride - A Versatile Fluorination Reagent

The nucleophilic reactivity of potassium fluoride was found to be appreciably enhanced via the despersion of KF onto an inert polymeric support.This crosslinked polystyrene was conveniently synthesized with high surface area and porosity.

Acceleration of the Fluorination of Benzyl Halide by the Combination of Lead Fluoride and Sodium Salt

A new composite reagent, a combination of lead fluoride (PbF2) and a small amount of sodium salt (NaX, X=F, Br etc.) was found to be useful for facilitating heterogeneous fluorination of substituted benzyl halides in acetonitrile.

Nucleophilic fluorination reactions starting from aqueous fluoride ion solutions

The sulfonium borane 2+ reacts with fluoride anions in MeOH/H2O mixtures to afford the zwitterionic fluoroborate 2-F as an easily isolable nonhygroscopic solid. In dry acetonitrile, 2-F reacts with PhS- to afford the anionic fluoroborate 1-F-. The latter is very labile and acts as a nucleophilic fluorination reagent toward a variety of substrates including alkylhalides and electron-deficient aromatic compounds. This approach may become broadly applicable to nucleophilic fluorination procedures that involve wet fluoride sources.

Tetraphenylphosphonium Hydrogendifluoride: a New Source of Fluoride Ion

Tetraphenylphosphonium hydrogendifluoride, a soluble and thermally stable reagent, acts as a source of fluoride ion in a variety of organic reactions.

Anhydrous tetrabutylammonium fluoride

Tetrabutylammonium fluoride (TBAF) is prepared at low temperature by nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide. Adventitious water is scavenged during this synthesis by the generated hexacyanobenzene, which readily adds water under basic conditions. Contrary to expectations, TBAF is stable to Hofmann elimination in polar aprotic solvents under anhydrous conditions. Added hydroxylic solvents are shown to catalyze the decomposition of TBAF and to catalyze proton exchange with DMSO. The synthetic utility of this salt is described briefly. Copyright