320-76-3

Basic information

• Product Name: 4-Bromo-2-fluoro-6-nitrophenol
• Synonyms: 4-BROMO-2-FLUORO-6-NITROPHENOL;4-Bromo-2-fluoro-6-nitrophenol 97%;4-Bromo-2-fluoro-6-nitrophenol97%;5-Bromo-3-fluoro-2-hydroxynitrobenzene, 5-Bromo-1-fluoro-2-hydroxy-3-nitrobenzene;5-Bromo-3-fluoro-2-hydroxynitrobenzene
• CAS NO: 320-76-3
• Molecular Formula: C₆H₃BrFNO₃
• Molecular Weight: 236
• Product Categories: Phenol&Thiophenol&Mercaptan;Heterocyclic Compounds;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 320-76-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 63-65 °C(lit.)
• Boiling Point: 241.372 °C at 760 mmHg
• Flash Point: 99.779 °C
• Appearance: white to light yellow crystal powder
• Density: 1.965 g/cm³
• Vapor Pressure: 0.0232mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.83±0.38(Predicted)
• CAS DataBase Reference: 4-Bromo-2-fluoro-6-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-fluoro-6-nitrophenol(320-76-3)
• EPA Substance Registry System: 4-Bromo-2-fluoro-6-nitrophenol(320-76-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 320-76-3(Hazardous Substances Data)

Usage

Description

4-Bromo-2-fluoro-6-nitrophenol is an organic compound characterized by its white to light yellow crystal powder appearance. It is a derivative of phenol, featuring a bromine atom at the 4th position, a fluorine atom at the 2nd position, and a nitro group at the 6th position in the aromatic ring. 4-Bromo-2-fluoro-6-nitrophenol is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-fluoro-6-nitrophenol is used as an intermediate compound for the preparation of Amino Pyrimidine compounds. These compounds are significant in the pharmaceutical industry due to their ability to inhibit protein Tyrosine kinase activity. Tyrosine kinases are enzymes that play a crucial role in cell signaling, and their inhibition can be beneficial in treating various diseases, including cancer.
The specific application of 4-Bromo-2-fluoro-6-nitrophenol in the pharmaceutical industry is to serve as a key building block in the synthesis of Amino Pyrimidine compounds. These compounds have been found to effectively inhibit the activity of protein Tyrosine kinases, which are often overactive in cancer cells, leading to uncontrolled cell growth and tumor formation. By targeting and inhibiting these enzymes, Amino Pyrimidine compounds can potentially slow down or stop the progression of cancer, making them valuable therapeutic agents.

InChI:InChI=1/C6H3BrFNO3/c7-3-1-4(8)6(10)5(2-3)9(11)12/h1-2,10H

Upstream product

• 576-86-3 2,4-dibromo-6-fluorophenol 
• 399-96-2 4-amino-2-fluorophenol 
• 403-19-0 2-fluoro-4-nitrophenol 
• 367-12-4 2-fluorophenol 
• 64-19-7 acetic acid 
• 2105-94-4 4-bromo-2-fluorophenol 

Downstream Products

• 182499-89-4 5-Bromo-3-fluoro-2-hydroxyaniline 
• 560082-53-3 6-bromo-8-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one 
• 943994-30-7 6-acetyl-8-fluoro-2H-1,4-benzoxazin-3(4H)-one 
• 1256255-94-3 6-bromo-8-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 943994-29-4 methyl 2-(4-bromo-2-fluoro-6-nitrophenoxy)acetate 
• 865716-56-9 2-(allyloxy)-5-bromo-1-fluoro-3-nitrobenzene 
• 74266-68-5 fluoro-3 methoxy-2 benzaldehhyde 
• 437-83-2 3-fluoro-2-methoxyaniline 
• 394-50-3 3-fluorosalicylaldehyde 
• 452912-13-9 2-(4-bromo-2-fluoro-6-nitro-phenoxy)-N,N-diisopropyl-acetamide 

Relevant articles and documents

Etude des complexes du cobalt (II) transporteurs d'oxygene: Nouvelle synthese du fluoro-3 hydroxy-2 benzaldehyde

Synthetic chelates of cobalt (II) derived from Schiff bases have remarkable behavior of reversibly absorbing and releasing molecular oxygene.Among these, bis (3-fluorosalicylaldehydeethylenediimide) Co (II) (fluomine: Formula A, X=F) is most interesting in allowing to isolate pure oxygen from air, because it absorbs with extreme rapidity 4.43percent of its weight of oxygen.Fluomine is easily prepared from 3-fluorosalicylaldehyde (3FSA), ethylenediamine and cobalt (II) chloride; but substances such as 3-substituted salicylaldehydes have proven to be extremely difficult to prepare in other than small laboratory quantities from the corresponding ortho-substituted phenol.Many author have prepared 3-fluorosalicylaldehyde, as described in patents, but often these syntheses are very long and the yields are generally less than 20percent.We now describe a new synthesis from o-fluorophenol.Nitration of o-fluorophenol with liquid nitrogen dioxide is convenient: - on the one hand, ortho-substitution to the hydroxyl group, is easy, -on the other hand, the para substituted by-product, is reinserted in the course of the synthesis, so that it is possible to minimize loss of the starting phenol, an expensive product. o-Fluorophenol 1 in solution in pentane, at about 0 deg C, is treated with liquid nitrogen dioxide (slight excess).The reaction is rapid and leads to 2-fluoro 6-nitrophenol 2 which remains in solution, and 2-fluoro 4-nitrophenol 7 which cristallizes rapidly (approximatively 50percent of each one). 2-Fluoro 6-nitrophenol 2 is converted into the anisole 3, the NO2 group of which is catalytically reduced by hydrogen into 3-fluoro 2-methoxy-aminobenzene 4.This amine 4 is diazotized, and treated with formaldoxime to lead to 3-fluoro 2-methoxybenzaldehyde 5 (Eb12 = 82 deg C). 3FSA is finally obtained by heating under reflux anisole 5 and a solution of hydrobromic acid (48percent). 2-Fluoro 4-nitrophenol 7 is converted in five steps into 3-fluoro 2-methoxyaminobenzene 4 by the same reactions as these used for its isomer.Finally the total yield of amine 4 from o-fluorophenol is 73percent, and 3FSA is obtained in 25percent yield.No primary amines are required during the isolation, so that no possible contamination of the final product is possible and therefore the fluomine prepared therefrom is not contaminated and deactivated.