ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluoronitrobenzene series 1-Bromo-4-fluoro-2-nitrobenzene

1-Bromo-4-fluoro-2-nitrobenzene

Product Name1-Bromo-4-fluoro-2-nitrobenzene
CAS446-09-3
MFC6H3BrFNO2
MW220
EINECS207-160-2
MOL File446-09-3.mol

Chemical Properties

Melting point	37-39°C
Boiling point	148-150°C 35mm
Density	1.808±0.06 g/cm3(Predicted)
Flash point	148-150°C/35mm
storage temp.	Sealed in dry,Room Temperature
form	powder to lump to clear liquid
color	White or Colorless to Yellow to Green
BRN	2364227
InChI	InChI=1S/C6H3BrFNO2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H
InChIKey	XRXNWKIKQFEOGO-UHFFFAOYSA-N
SMILES	C1(Br)=CC=C(F)C=C1[N+]([O-])=O
CAS DataBase Reference	446-09-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	20/21/22-36/37/38
Safety Statements	26-36/37/39-36/37
RIDADR	UN2811
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29049090

MSDS

Provider	Language
ALFA	English

Usage And Synthesis

Chemical Properties

light yellow powder

Uses

1-Bromo-4-fluoro-2-nitrobenzene serves as a reference for the analogous preparation of 2-bromo-4-fluoro-1-nitrobenzene[4]. The compound acts as a precursor in the synthesis of indole derivatives, including 7-bromo-4-fluoroindole, 4-fluoro-1H-indole-7-carbonitrile, and para-substituted precursors via linear pathways[4][5][8]. Furthermore, It functions as a reagent in coupling reactions with thiosalicylic acid or 5-chloro-2-aminobenzoic acid derivatives to produce substituted benzamides and benzoic acids[6][7].

Synthesis

394-01-4

446-09-3

General procedure for the synthesis of 2-bromo-5-fluoronitrobenzene from 2-nitro-4-fluorobenzoic acid: 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline, 37 mg of 2-nitro-4-fluorobenzoic acid, and 30.9 mg of sodium bromide were sequentially added to a Silak reactor tube fitted with a magnetic stirrer, followed by 4 mL of dimethyl sulfoxide as solvent. The reaction mixture was heated to 160°C under an oxygen atmosphere with continuous stirring for 24 hours. Upon completion of the reaction, distilled water was added to the reaction mixture to quench the reaction, followed by extraction with ethyl acetate three times at 10 mL each. the organic phases were combined, and 21.1 mg of 2-bromo-5-fluoronitrobenzene was obtained after concentration in 48% yield.

References

[1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A. Location in patent: Paragraph 0067
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
[4] Schlosser, M., Ginanneschi, A., Leroux, F. (2006). In Search of Simplicity and Flexibility: A Rational Access to Twelve Fluoroindolecarboxylic Acids. European Journal of Organic Chemistry, 2006(13), 2956–2969. https://doi.org/10.1002/ejoc.200600118
[5] Meuser, M. E., Rashad, A. A., Ozorowski, G., Dick, A., Ward, A. B., Cocklin, S. (2019). Field-Based Affinity Optimization of a Novel Azabicyclohexane Scaffold HIV-1 Entry Inhibitor. Molecules, 24(8), 1581. https://doi.org/10.3390/molecules24081581
[6] Sephton, S. M., Zhou, X., Thompson, S., Aigbirhio, F. I. (2019). Preparation of the Serotonin Transporter PET Radiotracer 2-({2-[(Dimethylamino)methyl]phenyl}thio)-5-[18F]fluoroaniline (4-[18F]ADAM): Probing Synthetic and Radiosynthetic Methods. Synthesis, 51(23), 4374–4384. https://doi.org/10.1055/s-0039-1690522
[7] Yang, T., Huhe, H., Williams, S., Kaur, S., Ay, Y. A., Davis‐Gilbert, Z. W., Cary, G. A., Paisie, C., Butler, R. R., Wiley, J., Betarbet, R., Fu, H., Duong, D., Seyfried, N. T., Leal, K., Carter, G. W., Edwards, A., Levey, A. I., Capener, J. L., … Center, T. E. T. (2025). PAK1 inhibitor NVS‐PAK1‐1 preserves dendritic spines in amyloid/tau exposed neurons and 5xFAD mice. Alzheimer's & Dementia, 21(12). https://doi.org/10.1002/alz.71033
[8] Weiss, P. S., Ermert, J., Meleán, J. C., Schäfer, D., Coenen, H. H. (2015). Radiosynthesis of 4-[18F]fluoro-l-tryptophan by isotopic exchange on carbonyl-activated precursors. Bioorganic & Medicinal Chemistry, 23(17), 5856–5869. https://doi.org/10.1016/j.bmc.2015.06.073

1-Bromo-4-fluoro-2-nitrobenzene

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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