2,4-Dibromoaniline
[CAS# 615-57-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2,4-Dibromoaniline
• Synonyms: 2,4-Dibromobenzenamine
• Molecular Formula: C₆H₅Br₂N
• Molecular Weight: 250.92
• CAS Registry Number: 615-57-6
• EC Number: 210-434-4
• SMILES: C1=CC(=C(C=C1Br)Br)N

Properties

• Density: 2.0±0.1 g/cm³, Calc.^*, 2.26 g/mL (Expl.)
• Melting point: 78-80 ºC (Expl.)
• Index of Refraction: 1.661, Calc.^*
• Boiling Point: 264.8±20.0 ºC (760 mmHg), Calc.^*, Boiling point|156 ºC (24 mmHg) (Expl.)
• Flash Point: 114.0±21.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H302-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

2,4-Dibromoaniline is an aromatic amine compound where two bromine atoms are attached to the benzene ring at the 2 and 4 positions relative to the amino group (-NH2). Its chemical formula is C6H4Br2NH2, and it appears as a white to light yellow solid with a characteristic odor. This compound belongs to the class of halogenated anilines, which have various applications in industries such as agrochemicals, pharmaceuticals, and dyes.

The discovery of 2,4-dibromoaniline arose from the ongoing study of halogenated aniline derivatives, a class of compounds recognized for their reactivity and versatility in organic synthesis. Like many aromatic amines, 2,4-dibromoaniline is synthesized by halogenation of aniline under controlled conditions. The most common synthesis method involves the bromination of aniline using bromine or a brominating agent such as NBS (N-Bromosuccinimide). This halogenation selectively introduces bromine atoms to the 2 and 4 positions on the aromatic ring due to the electron-donating nature of the amino group, which activates these positions for substitution. The resulting product, 2,4-dibromoaniline, is purified through recrystallization or other methods depending on the specific needs of the application.

2,4-Dibromoaniline has a wide array of applications due to its halogenated nature and the presence of the amino group, which makes it a useful intermediate in various chemical processes. One of the primary areas where 2,4-dibromoaniline is applied is in the synthesis of agrochemicals. The compound is used as an intermediate in the production of herbicides and fungicides. It can undergo further reactions, such as coupling with other chemicals, to form bioactive molecules that target specific pests or pathogens. The introduction of bromine atoms in the molecule enhances its chemical stability and bioactivity, making it suitable for use in formulations designed to protect crops from harmful organisms.

In addition to its agricultural applications, 2,4-dibromoaniline is also used in the synthesis of various pharmaceuticals. The compound serves as a key building block for the production of more complex molecules that exhibit antimicrobial, anti-inflammatory, or anticancer properties. Its structure allows for selective modifications that can introduce functional groups essential for biological activity, thus contributing to the development of new therapeutic agents. Researchers continue to explore the potential of 2,4-dibromoaniline in drug design, particularly in the creation of compounds that interact with specific biological targets.

Another notable application of 2,4-dibromoaniline is in the manufacture of dyes and pigments. The presence of the bromine atoms and the amino group on the benzene ring makes the compound highly reactive and capable of forming various colored complexes when combined with other chemical agents. It can be used in the preparation of dyes for textiles, plastics, and paper products, as well as in the creation of pigments for paints and coatings. The stability and color intensity of these dyes are enhanced by the halogenation of the aniline ring, making 2,4-dibromoaniline a valuable ingredient in the colorant industry.

Furthermore, 2,4-dibromoaniline is employed in organic synthesis, particularly in the formation of novel materials. It serves as a versatile intermediate in reactions such as nucleophilic substitution, coupling reactions, and cross-coupling reactions like the Suzuki and Heck reactions. These reactions are useful for creating complex organic compounds, including those with applications in electronics, materials science, and photochemistry. The compound’s ability to undergo various chemical transformations makes it an essential tool for chemists in the development of advanced materials and chemicals.

In conclusion, 2,4-dibromoaniline is a halogenated aromatic amine with significant industrial value, particularly in the fields of agrochemicals, pharmaceuticals, and dyes. Its synthesis and application have contributed to the development of numerous chemical products, and ongoing research continues to explore its potential in new applications. As the demand for more efficient and targeted chemical solutions grows, compounds like 2,4-dibromoaniline will play an increasingly important role in advancing chemical sciences.