1046785-21-0

Basic information

• Product Name: 4-(2-fluoro-1,1-dimethoxyethyl)-4-nitrobenzene
• CAS NO: 1046785-21-0
• Molecular Weight: 229.208
• Mol File: 1046785-21-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-(2-fluoro-1,1-dimethoxyethyl)-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-fluoro-1,1-dimethoxyethyl)-4-nitrobenzene(1046785-21-0)
• EPA Substance Registry System: 4-(2-fluoro-1,1-dimethoxyethyl)-4-nitrobenzene(1046785-21-0)

Safety Data

• Hazardous Substances Data: 1046785-21-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 350-39-0 p-Nitro-α-fluoroacetophenone 

Relevant articles and documents

Ruthenium-catalysed asymmetric transfer hydrogenation of para-substituted α-fluoroacetophenones

The first examples of asymmetric transfer hydrogenation of α-fluoroacetophenones are reported. Eight para-substituted α-fluoroacetophenones have been reduced using four catalytic systems constructed of [RuCl2(p-cymene)2]2 or [RuCl2(mesitylene)2]2 in combinations with each of the ligands (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine ((R,R)-TsDPEN) and (1R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexanediamine ((R,R)-TsCYDN). All reactions were performed in both water and formic acid/triethylamine. The highest enantioselectivity was obtained using the (R,R)-TsDPEN ligand in a formic acid/triethylamine mixture, giving the (S)-1-aryl-2-fluoroethanols in high to moderate enantiomeric excess (97.5-84.5%). For this solvent system the presence of electron withdrawing groups in the para position reduced the enantioselectivity. Reactions performed in water generally gave lower enantioselectivity and reaction rate, although RuCl(mesitylene)-(R,R)-TsDPEN yielded the product alcohols with enantiomeric excess in the range of 95.5-76.5%.

Electrophilic and nucleophilic side chain fluorination of para-substituted acetophenones

para-Substituted α-fluoroacetophenones have been synthesised by three different routes. Electrophilic fluorination of trimethylsilyl enol ethers of acetophenones using Selectfluor (F-TEDA-BF4, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) gave high to moderate yield depending on the electronic properties of the substituents. F-TEDA-BF4 mediated fluorination of acetophenones in methanol resulted in a mixture of α-fluoroacetophenones and the corresponding 2-fluoro-1,1-dimethyl acetals. The dimethyl acetals were hydrolysed using trifluoroacetic acid in water to maximise the yield of the product. Nucleophilic fluorination of α-bromoacetophenones using tetrabutylammonium hydrogen bifluoride (TBABF) led to moderate yield when having electron-donating substituents, whereas low yields were experienced when more electron-withdrawing substituents were introduced.