329045

Sigma-Aldrich

4-Fluoro-3-nitrobenzoic acid

98%

Linear Formula:
FC6H3(NO2)CO2H
CAS Number:
Molecular Weight:
185.11
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

98%

mp

123-126 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear, light yellow

SMILES string

OC(=O)c1ccc(F)c(c1)[N+]([O-])=O

InChI

1S/C7H4FNO4/c8-5-2-1-4(7(10)11)3-6(5)9(12)13/h1-3H,(H,10,11)

InChI key

BOJWTAQWPVBIPG-UHFFFAOYSA-N

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Application

4-Fluoro-3-nitrobenzoic acid was used:
  • as starting reagent in the preparation of novel benzimidazoles having antimycobacterial activity
  • in preparation of series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure
  • in preparation of bis(heterocyclic) skeletal precursors for the Pictet-Spengler reaction
  • in solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-diones

Packaging

5, 25 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Chih-Hau Chen et al.
Chemistry, an Asian journal, 6(6), 1557-1565 (2011-04-08)
A novel strategy for an unconventional Pictet-Spengler reaction has been developed for the regioselective cyclization of the imidazole ring system at the C2 position. The developed strategy was utilized to develop a diversity-oriented parallel synthesis for bis(heterocyclic) skeletal novel analogs...
Yeong Keng Yoon et al.
European journal of medicinal chemistry, 93, 614-624 (2014-07-06)
A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as (1)H NMR spectroscopic...
Yeong Keng Yoon et al.
Bioorganic chemistry, 49, 33-39 (2013-07-28)
Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by...
J C Wijkmans et al.
Molecular diversity, 3(2), 117-120 (1997-01-01)
4-Fluoro-3-nitrobenzoic acid attached to a solid support was shown to react under mild conditions with a wide range of functionalized phenols to yield, after cleavage, the corresponding biaryl ethers in excellent purity. In a similar fashion, biaryl thioethers could be...
Wen-Bing Yeh et al.
Combinatorial chemistry & high throughput screening, 7(3), 251-255 (2004-05-12)
Liquid phasel synthesis of biheterocyclic benzimidazoles by controlled microwave irradiation was investigated. Polymer immobilized o-phenylenediamines was synthesized under microwave irradiation. The resulting PEG bound diamines was N-acylated with 4-fluoro-3-nitrobenzoic acid selectively in primary aromatic amino moiety. Nucleophilic aromatic substitution of...

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