500-11-8

Usage

Uses

Used in Chemical Synthesis:
4-Nitrobenzylfluoride is used as an intermediate in the synthesis of various organic compounds, particularly those involving the benzyl group. Its reactivity allows for the formation of new chemical bonds and the creation of a wide range of products.
Used in Enzyme Inhibition Studies:
In biochemistry, 4-Nitrobenzylfluoride is employed as an inhibitor of serine proteases, a class of enzymes that play crucial roles in various biological processes. By acting as an inhibitor, it helps researchers understand the function and mechanism of these enzymes.
Used in Medicinal Chemistry:
4-Nitrobenzylfluoride is used as a building block in the development of new pharmaceuticals. Its unique structure and reactivity make it a valuable component in the design and synthesis of potential drug candidates.
Used in Investigating Reaction Mechanisms:
4-Nitrobenzyl fluoride is used in the investigation of electrostatic interaction between reacting fragments as the origin of the SN2 benzylic effect. This application helps researchers understand the underlying mechanisms of certain chemical reactions, which is essential for the development of new synthetic methods and the optimization of existing ones.

Upstream product

• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 619-73-8 4-nitrobenzyl chloride 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 
• 555-16-8 4-nitrobenzaldehdye 
• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 19479-80-2 (4-nitrophenyl)diazomethane 
• 24067-17-2 4-nitrophenylboronic acid 
• 373-53-5 fluoroiodomethane 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 81634-27-7 bis[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]sulfur difluoride 
• 350-50-5 benzyl fluoride 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 619-90-9 4-nitrobenzyl acetate 
• 62-23-7 4-nitro-benzoic acid 
• 51229-67-5 (α-Fluor-4-nitro-benzyl)-phenyl-sulfon 
• 6425-46-3 4-(4-nitrobenzyl)morpholine 
• 3145-86-6 4-nitrobenzyl iodide 
• 38695-23-7 1-(4-fluorobenzyl)-4-nitrobenzene 
• 1316859-67-2 4-(4-nitrobenzyl)-1,1'-biphenyl 
• 106731-06-0 1-methyl-3-(4-nitrobenzyl)benzene 
• 1817-77-2 4-benzyl-1-nitrobenzene 
• 736-30-1 1,2-bis(4-nitrophenyl)ethane 
• 39628-94-9 4-nitrobenzyl methanesulfonate 
• 100-14-1 4-nitrobenzyl chloride 
• 29848-57-5 4-(difluoromethyl)nitrobenzene 
• 51229-65-3 α-bromo-α-fluoro-4-nitrotoluene 

Relevant academic research and scientific papers

Organocatalysis Linked to Charge-Enhanced Acidity with Superelectrophilic Traits

Hydrogen bonding is ubiquitous throughout nature and serves as a versatile platform for accessing chemical reactivity. In leveraging this force, chemists have utilized organocatalysts to expand the spectrum of chemical reactivity enabled by hydrogen bondi

Deoxyfluorination of alcohols with aryl fluorosulfonates

Aryl fluorosulfonates are developed as a deoxyfluorinating reagent in the transformation of primary and secondary alcohols into the corresponding alkyl fluorides. These reagents feature easy availability, low-cost, high stability and high efficiency. Diverse functionalities including aldehyde, ketone, ester, halogen, nitro, alkene, and alkyne are well tolerated under mild reaction conditions.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group

Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.

Nucleophilic Substitution of Aliphatic Fluorides via Pseudohalide Intermediates

A method for aliphatic fluoride functionalization with a variety of nucleophiles has been reported. Carbon–fluoride bond cleavage is thermodynamically driven by the use of silylated pseudohalides TMS-OMs or TMS-NTf2, resulting in the formation of TMS-F and a trapped aliphatic pseudohalide intermediate. The rate of fluoride/pseudohalide exchange and the stability of this intermediate are such that little rearrangement is observed for terminal fluoride positions in linear aliphatic fluorides. The ability to convert organofluoride positions into pseudohalide groups allows facile nucleophilic attack by a wide range of nucleophiles. The late introduction of the nucleophiles also allows for a wide range of functional-group tolerance in the coupling partners. Selective alkyl fluoride mesylation is observed in the presence of other alkyl halides, allowing for orthogonal synthetic strategies.

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Expanding the repertoire of cyclopropenium ion phase transfer catalysis: Benzylic fluorination

The application of cyclopropenium ion as a phase transfer catalyst for benzylic fluorination in high yields is reported. Integral to the mechanisms of these fluorination reactions was the role of in situ derived cyclopropenium fluoride complexes, the existence of which was supported by 1H, 19F NMR and UV–Vis spectroscopy. Density functional theory calculations were applied to gain insight into the mechanism of these reactions.

Photochemical activation of SF6 by N-heterocyclic carbenes to provide a deoxyfluorinating reagent

The activation of the greenhouse gas SF6 using electron-rich N-heterocyclic carbenes gave 2,2-difluoroimidazolines or 2,2-difluoroimidazolidines as well as 2-thio derivatives of the carbene precursors. The N-heterocyclic carbenes can also convert SF4 to give similar products. The difluoroimidazolidine derivatives were applied in deoxyfluorination reactions. Furthermore, the activation of SF6 and the fluorination can be coupled in a one-pot process to convert 1-octanol into 1-fluorooctane.

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones

We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non-α-stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).