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 
• 619-73-8 4-nitrobenzyl chloride 
• 309-88-6 hexafluoropropene-diethylamine adduct 
• 75-61-6 dibromodifluoromethane 
• 619-25-0 3-Nitrobenzyl alcohol 
• 19479-80-2 (4-nitrophenyl)diazomethane 
• 99-99-0 1-methyl-4-nitrobenzene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 81634-27-7 bis[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]sulfur difluoride 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 
• 555-16-8 4-nitrobenzaldehdye 
• 373-53-5 fluoroiodomethane 

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

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.

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.