62406-72-8

Basic information

• Product Name: 2,4,6-Tribromo-3-nitroaniline
• Synonyms: 2,4,6-Tribromo-3-nitroaniline
• CAS NO: 62406-72-8
• Molecular Formula: C₆H₃Br₃N₂O₂
• Molecular Weight: 374.81222
• Mol File: 62406-72-8.mol

Chemical Properties

• Melting Point: 95-97°C
• Boiling Point: 319.3°C at 760 mmHg
• Flash Point: 146.9°C
• Appearance: /
• Density: 2.464g/cm³
• Vapor Pressure: 0.000342mmHg at 25°C
• Refractive Index: 1.72
• CAS DataBase Reference: 2,4,6-Tribromo-3-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Tribromo-3-nitroaniline(62406-72-8)
• EPA Substance Registry System: 2,4,6-Tribromo-3-nitroaniline(62406-72-8)

Safety Data

• Hazardous Substances Data: 62406-72-8(Hazardous Substances Data)

Usage

Chemical structure

2,4,6-Tribromo-3-nitroaniline consists of a benzene ring with two bromine atoms and one nitro group attached to it.

Physical appearance

It is a yellow crystalline solid.

Melting point

2,4,6-Tribromo-3-nitroaniline has a melting point of 202-205 degrees Celsius.

Molecular weight

The molecular weight of 2,4,6-Tribromo-3-nitroaniline is 357.87 g/mol.

Uses

It is commonly used as an intermediate in the synthesis of dyes and pigments, as well as in the manufacturing of pharmaceuticals and other organic compounds.

Laboratory applications

2,4,6-Tribromo-3-nitroaniline is also known for its use in laboratory research and analysis.

Environmental hazard

This chemical is classified as an environmental hazard and should be handled with care to avoid any harmful effects.

InChI:InChI=1/C6H3Br3N2O2/c7-2-1-3(8)6(11(12)13)4(9)5(2)10/h1H,10H2

Upstream product

• 24311-40-8 3-nitroaniline-6-sulphonic acid 
• 607-93-2 2,4,6-tribromoacetanilide 
• 99-09-2 3-nitro-aniline 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 67-66-3 chloroform 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 106-40-1 4-bromo-aniline 
• 5076-50-6 1,3-bis-(3-nitro-phenyl)-triazene 
• 53324-38-2 4-bromo-3-nitroaniline 

Downstream Products

• 3463-40-9 2,4,6-tribromonitrobenzene 
• 63561-49-9 N-(2,4,6-tribromo-3-nitro-phenyl)-diacetamide 

Relevant articles and documents

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.

An instant and facile bromination of industrially-important aromatic compounds in water using recyclable CaBr2-Br2 system

Various industrially-important brominated intermediates have been instantly synthesized using aq. CaBr2-Br2 system as an efficient and recyclable brominating reagent under aqueous conditions at room temperature without the need for metal catalysts or acidic additives. Structurally-diverse phenol and aniline derivatives with strong electron-withdrawing groups such as carboxylic, nitro and formyl show remarkable reactivity to the brominating reagent and brominated in 92-98% yield with high purity (>99%) in a very short reaction time. Organic solvent-free conditions, a feature of the green chemistry, were successively used not only for the reactions but also for the isolation of products at the end of the reaction. The recycling of HBr by its neutralization, thereby generating additional amounts of industrially-important CaBr2 has been designed and developed. The brominating reagent has been recycled and regenerated, and the process was repeated up to 4 cycles after the fresh batch using the regenerated brominating reagent having almost identical selectivity and isolated yields, which seems to be the most promising methodology from the viewpoint of the green approach to organic synthesis.

Effect of structural factors and solvent nature in bromination of anilines

Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.

Oxidative bromination of aniline and its derivatives

Oxidative bromination of aniline and its derivatives containing various substituents (CH3, Cl, NO2, COOH) in ortho, meta, and para positions with a brominating mixture of NaBr (KBr) and 20-22% hydrogen peroxide in 6-8% hydrochloric acid at the molar ratio aniline: NaBr (KBr): H 2O2: HCl = 1: 3.5: 3.2: 4.5 is described.

Regioselectivity of reductive debromination of substituted pentabromobenzenes with sodium tert-butoxide in DMSO

The regioselectivity of reductive debromination of substituted pentabromobenzenes C6Br5X (X = NH2, OMe, Me, H, Cl, F, and NO2) under the action of ButONa in DMSO containing ButOH has been studied. The reaction followed the halophilic mechanism via carbanions.

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2] octane tribromide as a highly reactive brominating agent for aniline derivatives

Reaction of anilines with 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide (3) in the presence of CaCO3 in small amounts of methanol gave brominated aromatic amines in good yields at room temperature. The isolation of products is straightforward.