15969-09-2

Basic information

• Product Name: 2,4-DIBROMO-6-NITROPHENOL
• Synonyms: 2,4-DIBROMO-6-NITROPHENOL;4,6-DIBROMO-2-NITROPHENOL;2-Nitro-4,6-dibromophenol;2,4-DIBROMO-6-NITROPHENO
• CAS NO: 15969-09-2
• Molecular Formula: C₆H₃Br₂NO₃
• Molecular Weight: 296.9
• Mol File: 15969-09-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 118 °C
• Boiling Point: 264.7 °C at 760 mmHg
• Flash Point: 113.9 °C
• Appearance: /
• Density: 2.247 g/cm³
• Vapor Pressure: 0.00585mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.52±0.38(Predicted)
• CAS DataBase Reference: 2,4-DIBROMO-6-NITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIBROMO-6-NITROPHENOL(15969-09-2)
• EPA Substance Registry System: 2,4-DIBROMO-6-NITROPHENOL(15969-09-2)

Safety Data

• Hazard Codes: Harmful:
• Hazardous Substances Data: 15969-09-2(Hazardous Substances Data)

Usage

General Description

2,4-Dibromo-6-nitrophenol is a synthetic organic compound that falls under the category of organobromines and phenols. It's a brominated derivative of nitrophenol and it has two bromine atoms (dibromo) and a nitro group (-NO2) attached to a phenol ring. The presence of three different substituents (two bromines and one nitro group) on the phenol ring makes it a versatile compound in organic synthesis. It is most commonly used in the manufacturing of dyes and pigments. Its physical properties include being yellow to brownish-yellow crystals with a strong odour. Handling it requires caution as it's toxic and harmful if swallowed, inhaled, or comes in contact with skin.

InChI:InChI=1/C6H3Br2NO3/c7-3-1-4(8)6(10)5(2-3)9(11)12/h1-2,10H

Upstream product

• 616-85-3 4-hydroxy-3-nitrobenzene sulfonic acid 
• 13073-25-1 2-bromo-6-nitro-phenol 
• 64-19-7 acetic acid 
• 88-75-5 2-hydroxynitrobenzene 
• 109-95-5 ethyl nitrite 
• 118-79-6 2,4,6-tribromophenol 
• 7726-95-6 bromine 
• 7727-15-3 aluminium bromide 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 615-58-7 2,4-dibromophenol 
• 7697-37-2 nitric acid 
• 29906-33-0 4-diazo-2-nitrophenol 
• 7732-18-5 water 

Downstream Products

• 121056-06-2 <3,5-(2)H2>-2-Hydroxyaniline 
• 35153-86-7 2,4-Dibrom-6-nitro-phenyl-iminocarbonat 
• 856632-74-1 2,4-dibromo-6-diazocyclohexa-2,4-dien-1-one 
• 79893-40-6 6-Amino-2,4-dibromoanisole 
• 6161-57-5 2,3,4,5-tetrabromo-6-nitrophenol 
• 6161-58-6 2-nitro-3,4,5,6-tetrabromoanisole 
• 6161-61-1 2,3,4,5-tetrabromoanisole 
• 725241-64-5 4,6-dibromo-2-nitroanisole 
• 55229-71-5 acetic acid-(2-bromo-4,6-dinitro-phenyl ester) 
• 87013-12-5 2-acetamido-6-bromo-1,4-benzoquinone 
• 857949-26-9 2-acetoxy-1-acetylamino-3,5-dibromo-benzene 
• 55202-09-0 2-acetamido-4,6-dibromophenol 
• 99-28-5 2,6-dibromo-4-nitrophenol 
• 488-48-2 tetrabromobenzoquinone 

Relevant articles and documents

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water

The mildly acidic and oxidative nature of graphene oxide, with its large surface area available for catalytic activity, has been explored in aromatic nuclear bromination chemistry for the first time. The versatile catalytic activity of graphene oxide (GO) has been used to selectively and rapidly brominate anilines and phenols in water. The best results were obtained at ambient temperatures using molecular bromine in a protocol promoted by oxidative bromination catalyzed by GO; these transformations proceeded with 100% atom economy with respect to bromine and high selectivities for the tribromoanilines and -phenols. Reduced graphene oxide (r-GO) was observed to form after the second recycle (third use) of GO. This technique is also effective with N-bromosuccinimide (NBS) as the brominating reagent. In the case of NBS, reactions were instantaneous and the GO displayed excellent recyclability without any loss of activity over several cycles.

Fast and efficient bromination of aromatic compounds with ammonium bromide and Oxone

A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. Georg Thieme Verlag Stuttgart . New York.