5847-59-6

Basic information

• Product Name: 2-Bromo-4-nitrophenol
• Synonyms: 2-BROMO-4-NITROPHENOL;4-Hydroxy-3-bromonitrobenzene;2-Bromo-4-nitropheno;Phenol,2-broMo-4-nitro-;2-Bromo-4-nitrophenol >=98.0%
• CAS NO: 5847-59-6
• Molecular Formula: C₆H₄BrNO₃
• Molecular Weight: 218
• EINECS: 1533716-785-6
• Mol File: 5847-59-6.mol
• Article Data: 62

Chemical Properties

• Melting Point: 111-115 °C
• Boiling Point: 298.1 °C at 760 mmHg
• Flash Point: 134.1 °C
• Appearance: /
• Density: 1.8994 (rough estimate)
• Vapor Pressure: 0.000729mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 5.36±0.22(Predicted)
• Water Solubility: 22g/L(100 oC)
• BRN: 2441518
• CAS DataBase Reference: 2-Bromo-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-nitrophenol(5847-59-6)
• EPA Substance Registry System: 2-Bromo-4-nitrophenol(5847-59-6)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 5847-59-6(Hazardous Substances Data)

Usage

General Description

2-Bromo-4-nitrophenol is a chemical compound with the molecular formula C6H4BrNO3. It is a yellow crystalline solid that is soluble in water and organic solvents. 2-Bromo-4-nitrophenol is used in the synthesis of pharmaceuticals and other organic compounds. It is also used as a reagent in organic chemistry reactions, particularly in the synthesis of dyes and other fine chemicals. Additionally, 2-Bromo-4-nitrophenol has been studied for its potential antimicrobial and antifungal properties, making it a potential candidate for use in medicinal and agricultural applications. Due to its reactivity and potential health hazards, proper safety protocols should be followed when handling and using this compound in laboratory and industrial settings.

InChI:InChI=1/C6H4BrNO3/c7-5-3-4(8(10)11)1-2-6(5)9/h1-3,9H

Upstream product

• 100-02-7 4-nitro-phenol 
• 95-56-7 2-hydroxybromobenzene 
• 15516-58-2 2-bromo-4-nitroso-phenol 
• 58244-42-1 2-bromo-1-ethoxy-4-nitrobenzene 
• 855836-08-7 5-amino-2-bromo-4-nitro-phenol 
• 64-19-7 acetic acid 
• 585-79-5 m-nitrobromobenzene 
• 7726-95-6 bromine 
• 15969-09-2 2,4-dibromo-6-nitrophenol 
• 7732-18-5 water 
• 13362-37-3 bromo-[1,4]benzoquinone-4-oxime 
• 63801-96-7 2-bromo-4-nitrophenyl acetate 
• 536-74-3 phenylacetylene 
• 7486-35-3 tri-n-butyl(vinyl)tin 

Downstream Products

• 63801-96-7 2-bromo-4-nitrophenyl acetate 
• 84174-71-0 7-bromo-6-quinolinol 
• 115581-09-4 5-bromo-6-hydroxyquinoline 
• 5197-28-4 2-bromo-4-nitroanisole 
• 79807-54-8 potassium 2-bromo-4-nitrophenoxide 
• 177597-23-8 2-bromo-1-(2-bromoethoxy)-4-nitrobenzene 
• 191602-86-5 1-(benzyloxy)-2-bromo-4-nitrobenzene 
• 191602-42-3 2-bromo-1-isopropoxy-4-nitrobenzene 
• 83189-97-3 2-bromo-1-difluoromethoxy-4-nitro-benzene 
• 373380-62-2 2-bromo-1-(methoxymethoxy)-4-nitrobenzene 
• 744196-30-3 4-Amino-2-phenoxy-phenol 

Relevant articles and documents

New procedure for the highly regioselective aerobic bromination of aromatic compounds using copper-based nanocatalyst

A new procedure for the highly regioselective aerobic bromination of aromatic compounds in the presence of copper-based nanoparticles (CuO/ZnO nanocatalyst) under reflux condition is described. Mechanistic parameters are discussed and the plausible mechanism is proposed. Recyclability of the CuO/ZnO nanocatalyst has also been explored upon aerobic bromination of aromatic compounds.

Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin

Kosugi-Migita-Stille cross coupling reactions of (ethenyl)tributyltin with all isomeric permutations of bromophenyl triflate and bromo-nitrophenyl triflate were examined in order to determine the chemoselectivity of carbon-bromine versus carbon-triflate bond coupling under different reaction conditions. In general, highly selective carbon-bromine bond cross couplings were observed using for example bis(triphenylphosphine)palladium dichloride (2 mol-%) in 1,4-dioxane at reflux. In contrast, reactions using the same pre-catalyst but in the presence of a three-fold excess of lithium chloride in N,N-dimethylformamide at ambient temperature were in most cases selective for coupling at the carbon-triflate bond. Overall, isolated yields and the selectivity for carbon-bromine bond coupling were significantly higher compared to carbon-triflate bond coupling.

o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols

Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.