455-93-6

Usage

Uses

Used in Biochemical Research:
2-Fluoro-4-nitroanisole is used as an alternative biochemical photoprobe for proteins. It aids in the study of protein interactions and mechanisms, providing valuable insights into protein structure and function.
Used in Chemical Synthesis:
2-Fluoro-4-nitroanisole can be utilized as a key intermediate in the synthesis of various organic compounds, particularly those requiring a fluorinated aromatic moiety. Its unique chemical properties make it a valuable building block in the development of new pharmaceuticals and specialty chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 8448, 1998 DOI: 10.1021/jo981557o

InChI:InChI=1/C7H7FN2O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,9H2,(H,10,11)

Upstream product

• 321-28-8 1-fluoro-2-methoxybenzene 
• 100-17-4 para-methoxynitrobenzene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 369-34-6 3,4-difluoronitrobenzene 
• 99-59-2 3-amino-4-methoxynitrobenzene 
• 403-20-3 3-fluoro-p-anisic acid 
• 1825-61-2 Trimethylmethoxysilane 
• 403-19-0 2-fluoro-4-nitrophenol 
• 367-11-3 ortho-difluorobenzene 
• 350-31-2 1-chloro-2-fluoro-4-nitrobenzene 
• 124-41-4 sodium methylate 

Downstream Products

• 452-15-3 N-(3-fluoro-4-methoxyphenyl)acetamide 
• 709-09-1 3,4-dimethoxynitrobenzene 
• 636-93-1 5-nitroguaiacol 
• 65739-04-0 (2-fluoro-4-nitro-phenyl)-dimethyl-amine 
• 7501-46-4 N,N-dimethyl-2-methoxy-5-nitroaniline 
• 124431-92-1 N-methyl-2-fluoro-4-nitroaniline 
• 124431-95-4 N-hexyl-2-fluoro-4-nitroaniline 
• 114568-54-6 N-(1-hexyl)-2-methoxy-5-nitroaniline 
• 124431-93-2 N-butyl-2-fluoro-4-nitroaniline 
• 93398-03-9 N-butyl-2-methoxy-5-nitroaniline 
• 19871-39-7 N-methyl-2-methoxy-5-nitroaniline 
• 91214-97-0 N-ethoxycarbonylmethyl-2-methoxy-5-nitroaniline 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 331-62-4 3-fluoro-4-methoxybenzonitrile 

Relevant academic research and scientific papers

Anodic fluorination of 4-methoxy-1-naphthol and 4-nitroanisole using Et3N · 5 HF in mixed nonaqueous solvent

Anodic fluorination of 4-methoxy-1-naphthol and 4-nitroanisole has been investigated in a mixed nonaqueous solvent using Et3N · 5 HF as supporting electrolyte as well as fluorine source. In order to avoid the formation of polymer on the anode,

Base-promoted nucleophilic fluoroarenes substitution of C–F bonds

With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.

Method for preparing alkyloxy aromatic compound from fluoroaromatic compound

The invention discloses a method for preparing an alkyloxy aromatic compound from a fluoroaromatic compound. The alkyloxy aromatic compound is highly-efficiently prepared through a reaction of the fluoroaromatic compound, a strong alkali, dimethyl sulfoxide and alcohol under certain conditions. The method has the advantages of no metal catalyst, mild and controllable reaction, simple process, good universality, and suitableness for large-scale industrial production.

Constructing a catalytic cycle for c-f to c-x (x = o, s, n) bond transformation based on gold-mediated ligand nucleophilic attack

A tricoordinated gold(I) chloride complex, tBuXantphosAuCl, supported by a sterically bulky 9,9-dimethyl-4,5-bis(di-Tert-butylphosphino)xanthene ligand (tBuXantphos) was synthesized. This complex features a remarkably longer Au?Cl bond length [2.632(1) ?] than bicoordinated linear gold complexes (2.27-2.30 ?) and tricoordinated XantphosAuCl [2.462(1) ?]. Single-crystal Xray diffraction analysis of a cocrystal of tBuXantphosAuCl and pentafluoronitrobenzene (PFNB) and UV-vis spectroscopic titration experiments revealed the existence of an anion-φ interaction between the Cl anion ligand and PFNB. Stoichiometric reaction between PFNB and tBuXantphosAuOtBu, after replacement of Cl by a more nucleophilic tBuO anion ligand, showed higher reactivity and para selectivity in the transformation of C-F to C-OtBu bond, distinctively different from that when only KOtBu was used (ortho selectivity) under the identical condition. Mechanistic studies including density functional theory calculations suggested a gold-mediated nucleophilic ligand attack of the C?F bond pathway via an SNAr process. On the basis of these results, using trimethylsilyl derivatives TMS-X (X = OMe, SEt, NEt) as the nucleophilic ligand source and the fluorine acceptor, catalytic transformation of the C-F bond of aromatic substrates to the C-X (X = O, S, N) bond was achieved with tBuXantphosAuCl as the catalyst (up to 20 turnover numbers).

Fluorination of aromatic compounds with xenon difluoride in the presence of boron trifluoride etherate

Fluorination of benzene with the XeF2 - BF3?Et2O system in acetonitrile at low temperatures affords fluorobenzene in 18% yield, the conversion of benzene being 92%. The rest products are di-, tri-, tetra-, and polyphenyls with different fluorination pattern. Toluene and chloro- and bromobenzenes are fluorinated predominantly at the ortho and para positions. Fluorination of 4-nitroanisole affords 2-fluoro-4-nitroanisole in 73% yield.

Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate

A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.

Elemental fluorine. Part 20. Direct fluorination of deactivated aromatic systems using microreactor techniques

Continuous flow microreactor technology has been used for the direct fluorination of a range of deactivated di- and tri-substituted aromatic systems.

Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them

The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.

Tandem of nucleophilic substitution of hydrogen and cyclocondensation with participation of nitro group in the synthesis of fluorine-containing 3-amino-1,2,4-benzotriazines

Reactions of 3-fluoro-1-nitrobenzenes with guanidine hydrochloride in THF in the presence of ButOK gave isomeric 5-and 7-fluoro-containing 3-amino-1,2,4-benzotriazines. Springer Science+Business Media, Inc. 2006.

Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines

A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 5-HT(1A) agonist activity and in vitro radioligand competition assays for their affinity at 5-HT(2A), 5-HT(2C), and 5-HT(1A) receptor sites. Functional activity at the 5-HT(2A) receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT(1A) receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT(1A) agonist activity, with potency greater than that of the 5-HT(1A) agonist 8-OH-DPAT. The ED50 of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT(1A) agonist LY293284 was 0.17μmol/kg, and the K(i) at [3H]8-OH-DPAT-labeled 5-HT(1A) receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT(2A/2C) receptor affinity or intrinsic activity. Affinity at the 5-HT(1A) receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT(1A) receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT(2A) receptor activation, the present results suggest a possible role for involvement of the 5-HT(1A) receptor with tryptamines.