Production Method 1

13296-94-1

827-94-1

Reaction Conditions

1.1 Catalysts: Copper sulfate Solvents: Acetonitrile ,  Water ;  15 min, 25 °C
1.2 Reagents: Sodium bromide ,  Sodium persulfate ;  15 min, 7 °C; 2 h, 7 °C; 22 h, 25 °C
1.3 Reagents: Sodium hydroxide ,  Sodium thiosulfate Solvents: Water ;  pH 9

Reference

A Practical Procedure for Regioselective Bromination of Anilines

Takahashi, Yusuke; et al, Synthesis, 2021, 53(10), 1828-1832

Production Method 2

13296-94-1

827-94-1

Reaction Conditions

1.1 Reagents: Hydrogen peroxide ,  Potassium bromide Catalysts: Polyacrylonitrile (dioxo(peroxo)molybdenum bonded) ,  Molybdenum oxide peroxide (MoO2(O2)), (T-4)- (polyacrylonitrile-anchored) Solvents: Acetonitrile ,  Water ;  1 h, rt

Reference

Polymer-anchored peroxo compounds of molybdenum and tungsten as efficient and versatile catalysts for mild oxidative bromination

Boruah, Jeena Jyoti; et al, Polyhedron, 2013, 52, 246-254

Production Method 3

13296-94-1

827-94-1

Reaction Conditions

1.1 Reagents: Tetraethylammonium bromide ,  Vanadate(3-), dioxotetraperoxy[μ-(2-propenoato-κO:κO′)]di-, sodium (1:3), homopo… (resin bound) Solvents: Acetonitrile ,  Water ;  7 h, rt

Reference

Synthesis, characterization, reactivity and antibacterial activity of new peroxovanadium(V) complexes anchored to soluble polymers

Kalita, Diganta; et al, Reactive & Functional Polymers, 2008, 68(4), 876-890

2-Bromo-4-nitroaniline Preparation Products

• 2-Bromo-4-nitroaniline (13296-94-1)
• 2,6-Dibromo-4-nitroaniline (827-94-1)

• 1. 267. A reaction of certain diazosulphonates derived from β-naphthol-1-sulphonic acid. Part XII. Preparation of phthalazine, phthalazone, and phthalimidine derivatives from 2-bromo-4-nitroaniline
  F. M. Rowe,G. B. Jambuserwala,H. W. Partridge J. Chem. Soc. 1935 1134
• 2. 267. A reaction of certain diazosulphonates derived from β-naphthol-1-sulphonic acid. Part XII. Preparation of phthalazine, phthalazone, and phthalimidine derivatives from 2-bromo-4-nitroaniline
  F. M. Rowe,G. B. Jambuserwala,H. W. Partridge J. Chem. Soc. 1935 1134
• 3. Notes
  Morna Macleod,Charles Stanley Gibson,John Dobney Andrew Johnson J. Chem. Soc. 1928 3092
• 4. Notes
  Morna Macleod,Charles Stanley Gibson,John Dobney Andrew Johnson J. Chem. Soc. 1928 3092
• 5. Organic chemistry
  J. Chem. Soc. Abstr. 1913 104 i949

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzenes
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 2-Bromo-4-nitroaniline (CAS No. 13296-94-1)

2-Bromo-4-nitroaniline (CAS No. 13296-94-1) is a versatile organic compound that has garnered significant attention in the fields of chemistry, biology, and pharmaceutical research. This compound, characterized by its unique molecular structure, has found applications in various areas, including the synthesis of dyes, intermediates for pharmaceuticals, and as a precursor in the development of novel materials. This comprehensive introduction aims to provide an in-depth understanding of the properties, synthesis methods, and potential applications of 2-Bromo-4-nitroaniline.

Molecular Structure and Properties

2-Bromo-4-nitroaniline is a substituted aniline derivative with the molecular formula C₆H₅BrN₂O₂. The compound features a benzene ring with a bromine atom at the 2-position and a nitro group at the 4-position. The presence of these functional groups imparts distinct chemical properties to the molecule. The bromine atom is an excellent leaving group, making 2-Bromo-4-nitroaniline highly reactive in nucleophilic substitution reactions. The nitro group, on the other hand, introduces electron-withdrawing effects, which can influence the reactivity and stability of the molecule.

The physical properties of 2-Bromo-4-nitroaniline include a melting point of approximately 105°C and a boiling point of around 300°C. It is slightly soluble in water but exhibits good solubility in organic solvents such as ethanol and acetone. These properties make it suitable for various synthetic processes and analytical techniques.

Synthesis Methods

The synthesis of 2-Bromo-4-nitroaniline can be achieved through several routes, each with its own advantages and limitations. One common method involves the nitration of 2-bromophenylamine using a mixture of nitric acid and sulfuric acid. This reaction typically proceeds via electrophilic aromatic substitution, where the nitronium ion (NO₂₊) attacks the benzene ring at the para position relative to the amino group.

An alternative approach involves the bromination of 4-nitroaniline using bromine or N-bromosuccinimide (NBS) in an appropriate solvent. This method is particularly useful for controlling regioselectivity and minimizing side reactions. Recent advancements in green chemistry have also led to the development of more environmentally friendly synthesis methods, such as using microwave-assisted reactions or catalytic systems that reduce waste generation.

Analytical Techniques

The characterization of 2-Bromo-4-nitroaniline is crucial for ensuring its purity and suitability for various applications. Common analytical techniques used for this purpose include nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and infrared (IR) spectroscopy.

NMR spectroscopy provides detailed information about the molecular structure by analyzing the chemical shifts and coupling constants of hydrogen and carbon atoms. MS is particularly useful for determining the molecular weight and identifying any impurities or by-products. IR spectroscopy can be used to confirm the presence of specific functional groups, such as the nitro group and amino group.

Potential Applications

2-Bromo-4-nitroaniline has found applications in various fields due to its unique chemical properties. In the dye industry, it serves as an intermediate for the synthesis of azo dyes, which are widely used in textile coloring and printing processes. The reactivity of the bromine atom makes it an excellent starting material for further functionalization, leading to a wide range of derivatives with diverse applications.

In pharmaceutical research, 2-Bromo-4-nitroaniline has been explored as a precursor for synthesizing potential drug candidates. Recent studies have shown that derivatives of this compound exhibit promising biological activities, including antimicrobial and anticancer properties. For example, a study published in the Journal of Medicinal Chemistry reported that certain derivatives of 2-Bromo-4-nitroaniline demonstrated significant inhibition against cancer cell lines while showing low toxicity to normal cells.

Beyond its use in dyes and pharmaceuticals, 2-Bromo-4-nitroaniline has also been investigated for its potential in materials science. Researchers have explored its use as a building block for constructing advanced materials with unique optical and electronic properties. For instance, a study published in Advanced Materials highlighted the synthesis of conjugated polymers using derivatives of 2-Bromo-4-nitroaniline strong>, which exhibited excellent photoluminescence and charge transport characteristics.

Safety Considerations

Safety is a critical aspect when handling any chemical compound. While specific safety data sheets (SDS) should always be consulted for detailed information, it is generally advisable to handle 2-Bromo-4-nitroaniline strong > with appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats. The compound should be stored in a cool, dry place away from incompatible materials.

In conclusion, 2-Bromo-4-nitroaniline (CAS No. 13296-94-1) strong > is a valuable compound with a wide range of applications in chemistry, biology, and pharmaceutical research. Its unique molecular structure and reactivity make it an essential building block for synthesizing various derivatives with diverse functionalities. Ongoing research continues to uncover new potential uses for this compound, further highlighting its significance in modern scientific endeavors.

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