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4-Fluoro-3-nitrobenzoic acid

Name: 4-Fluoro-3-nitrobenzoic acid
Brand: ALDRICH

98%

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Linear Formula:

FC₆H₃(NO₂)CO₂H

CAS Number:

453-71-4

Molecular Weight:

185.11

EC Number:

207-221-3

MDL number:

MFCD00007058

PubChem Substance ID:

24859766

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

GHS07

Signal Word

Warning

Hazard Statements

H302 - H315 - H319 - H335

Precautionary Statements

P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Regioselective, unconventional Pictet-Spengler cyclization strategy toward the synthesis of benzimidazole-linked imidazoquinoxalines on a soluble polymer support.

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

Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors.

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

Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters.

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

Solid phase synthesis of functionalized biaryl ethers: versatile scaffolds for combinatorial chemistry.

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

Combinatorial synthesis of biheterocyclic benzimidazoles by microwave irradiation.

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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