500-11-8

Basic information

• Product Name: 4-Nitrobenzylfluoride
• Synonyms: 4-Nitrobenzylfluoride
• CAS NO: 500-11-8
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.1264432
• Mol File: 500-11-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 38.5 °C
• Boiling Point: 110-115 °C(Press: 18 Torr)
• Appearance: /
• Density: 1.260±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-Nitrobenzylfluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzylfluoride(500-11-8)
• EPA Substance Registry System: 4-Nitrobenzylfluoride(500-11-8)

Safety Data

• Hazardous Substances Data: 500-11-8(Hazardous Substances Data)

Usage

Uses

4-Nitrobenzyl fluoride is used in the investigation of electrostatic interaction between reacting fragments as origin of SN2 benzylic effect.

Upstream product

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

Downstream Products

• 3048-12-2 4-nitrobenzyl phenyl ether 
• 100-14-1 4-nitrobenzyl chloride 
• 619-90-9 4-nitrobenzyl acetate 
• 51229-65-3 α-bromo-α-fluoro-4-nitrotoluene 
• 29848-57-5 4-(difluoromethyl)nitrobenzene 
• 62-23-7 4-nitro-benzoic acid 
• 51229-67-5 (α-Fluor-4-nitro-benzyl)-phenyl-sulfon 
• 6425-46-3 4-(4-nitrobenzyl)morpholine 
• 39628-94-9 4-nitrobenzyl methanesulfonate 
• 1817-77-2 4-benzyl-1-nitrobenzene 
• 736-30-1 1,2-bis(4-nitrophenyl)ethane 
• 106731-06-0 1-methyl-3-(4-nitrobenzyl)benzene 
• 1316859-67-2 4-(4-nitrobenzyl)-1,1'-biphenyl 
• 38695-23-7 1-(4-fluorobenzyl)-4-nitrobenzene 

Relevant articles and documents

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 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.