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Sigma-Aldrich

4-Fluoro-3-nitrobenzoic acid

98%

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About This Item

Linear Formula:
FC6H3(NO2)CO2H
CAS Number:
453-71-4
Molecular Weight:
185.11
EC Number:
207-221-3
MDL number:
MFCD00007058
UNSPSC Code:
12352100
PubChem Substance ID:
24859766
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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.
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
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
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
Gérard Klein et al.
Journal of combinatorial chemistry, 4(4), 345-351 (2002-07-09)
An efficient method for the solid-phase synthesis of trisubstituted [1,3,5]triazino[1,2-a]benzimidazole-2,4(3H,10H)-diones from resin-bound amino acids is described. N-acylation of the primary amine of a resin-bound amino acid with 4-fluoro-3-nitrobenzoic acid, followed by displacement of the fluoro group and reduction of the
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