2-Amino-6-bromopyridine CAS 19798-81-3

2-Amino-6-bromopyridine demonstrates unique value beyond conventional organic synthesis: the intramolecular N-H...N hydrogen bond forms a pseudo-six-membered ring structure, significantly influencing the charge distribution and vibration spectrum of the molecule, resulting in a specific proton transfer barrier in the solid state. This makes it a model compound for studying intramolecular hydrogen bond dynamics. In coordination chemistry, this molecule is an atypical "claw-shaped" precursor, where the amino group and bromine atom can cooperatively coordinate with the metal center to form a distorted chelate. These complexes exhibit unconventional regioselectivity in catalyzing C-X bond activation. In recent years, it has been used in materials science to construct fluorescent groups with excited-state intramolecular proton transfer effects. The bromine atom allows precise control of the luminescence properties through coupling reactions, while the amino group provides the site for forming hydrogen-bonded organic frameworks, creating crystalline materials with anisotropic proton conduction capabilities. Additionally, in the field of nonlinear optics, its molecular asymmetry and polarity make it a potential building block for preparing organic second-order nonlinear optical materials. Through the functionalization of the bromine atom, supermolecular polarization arrangements can be achieved. This compound is also used as a dual-labeling carrier in isotope labeling studies, using the bromine atom and amino group to introduce radioactive or stable isotopes respectively for tracking complex biological transformation pathways. These unconventional applications highlight its potential as a multifunctional platform, far exceeding its traditional understanding as a common synthetic intermediate.

2-Amino-6-bromopyridine, also known as Aminobromopyridine or 6-bromo-2-pyridinamine, is a significant chemical compound within the pyridine derivatives, characterized by its molecular formula C5H6BrN2 and molecular weight of 174.018. This compound exists as a shallow yellow to light brown powder at room temperature and pressure, possessing a melting point range of 88-93°C.

In the field of pharmaceutical synthesis, it has found practical application, particularly in the synthesis of anti-HIV drugs. It serves as a crucial intermediate in organic and medicinal chemistry, enabling the formation of structural fragments vital for antiviral compounds. One notable example is its role in the synthesis of 7-azaindole, a structural segment found in anti-HIV medications. This contribution underscores its importance in the development of treatments aimed at combating HIV.

Moreover, it exhibits solubility in polar organic solvents such as N,N-dimethylformamide but displays poor solubility in non-polar solvents like chloroform and dichloromethane, and is insoluble in water. These properties facilitate its utilization in specific synthetic pathways where controlled solubility is crucial.

The incorporation of 2-Amino-6-bromopyridine in anti-HIV drug synthesis not only expands the range of therapeutic options but also underscores the versatility of pyridine derivatives in medicinal chemistry. By enabling the creation of potent antiviral agents, this compound contributes to advancements in HIV treatment, offering hope for patients worldwide. In summary, its practical application in synthesizing anti-HIV drugs highlights its pivotal role in the pharmaceutical industry, demonstrating its value in addressing significant health challenges.

 

 

Chemical Properties and Potential Hazards

2-amino-6-bromopyridine is a nitrogen-containing heterocyclic compound with the molecular formula C₅H₅BrN₂ and a molecular weight of 174.018. At room temperature, it is a light yellow to light brown solid powder with a melting point of 88-91°C and a boiling point of 273°C. The amino group (-NH₂) and bromine atom (-Br) in its chemical structure endow it with reactivity, and it may participate in oxidation, reduction or substitution reactions. This substance poses a slight hazard to water bodies. It is strictly prohibited to discharge it into the environment without permission. Waste must be treated in accordance with the standards for hazardous chemicals.

Environmental Risk Assessment

 

Hazards of water bodies

This substance is slightly toxic to aquatic organisms and may disrupt the ecological balance of water bodies. If discharged without treatment, it may pollute rivers, lakes or groundwater.

Soil pollution

Leakage or improper disposal may lead to residues in the soil, affecting microbial activity or plant growth. It should be treated in accordance with the standards for hazardous waste and should not be landfilled or discarded at will.

Ecotoxicity

There is a lack of detailed ecotoxicity data, but as an organic synthesis intermediate, its use and discharge need to be strictly controlled to prevent accumulation through the food chain.

 

 

Storage and Waste Management

Storage conditions

Store in a sealed container in a cool and dry place, away from damp environments to prevent moisture absorption and caking.

The recommended storage temperature is room temperature (20-25°C), and it should be kept away from strong acids, strong alkalis or oxidants.

Containers should be marked with the name of the chemical, CAS number (19798-81-3) and hazard identification.

Waste disposal

It is prohibited to discharge directly into the sewer or ordinary garbage bins. It should be treated in accordance with the standards for hazardous chemicals.

Contact professional environmental protection agencies or follow local regulations for disposal through high-temperature incineration or chemical neutralization, and keep records of the treatment.

2-Amino-6-bromopyridine is a nitrogen-containing heterocyclic compound. Its chemical stability is influenced by various factors. The following analyzes its stability from different perspectives:

2-Amino-6-bromopyridine is a light yellow to pale brown solid powder at room temperature and normal pressure. Its melting point is 88-91°C, its boiling point is 273°C (760 mmHg), and its flash point is 118.9°C. This indicates that the substance has relatively high thermal stability at room temperature, but it may decompose or volatilize under high-temperature conditions. Therefore, when storing, direct contact with open flames or high-temperature sources should be avoided to prevent combustion or decomposition reactions.

2-Amino-6-bromopyridine can be stored stably for a long time in a sealed, cool and dry environment. Its storage stability is affected by the following factors:

Hygroscopicity: This substance may absorb moisture and form lumps, which may affect its purity and performance. Therefore, it should be stored in an airtight container to prevent contact with humid environments.

Chemical compatibility: It should be avoided from coming into contact with strong oxidants, strong acids, or strong bases to prevent exothermic reactions or the generation of toxic gases. For example, mixing with strong oxidants may cause a violent reaction, even explosion.

Light influence: Long-term exposure to light may lead to the decomposition of the substance. Therefore, it is recommended to store it in a dark environment.

The amino group (-NH₂) and bromine atom (-Br) in the 2-amino-6-bromopyridine molecule give it high reactivity, which may participate in various chemical reactions:

Oxidation reaction: In the presence of strong oxidants, an oxidation reaction may occur, generating toxic substances such as nitrogen oxides or bromides.

Substitution reaction: The bromine atom may be replaced by other groups, resulting in the formation of new compounds.

Acid-base reaction: The amino group has basic properties and may undergo neutralization reactions with acids, generating salts.

To enhance the chemical stability of 2-amino-6-bromopyridine, the following measures can be taken:

Optimize storage conditions: Store in a sealed manner in a cool, dry, and dark environment, avoiding coexistence with oxidants, acids, and bases.

Control the operating environment: Perform operations in a fume hood or local exhaust equipment to reduce dust dispersion. During operation, avoid using high-pressure air streams or vigorous stirring to prevent the generation of aerosols.

Use stabilizers: In specific application scenarios, add stabilizers to inhibit the occurrence of side reactions and extend the service life of the substance.

1. What is 2-amino-6-bromopyridine?
It is an important organic synthetic intermediate with the chemical formula C₅H₅BrN₂. Its structure features an amino group (-NH₂) at the 2-position and a bromine atom (-Br) at the 6-position of the pyridine ring.
2. What are the main applications?
It is mainly used for the synthesis of pharmaceutical and pesticide molecules, such as as a key component for constructing heterocyclic compounds; it is also used in ligand synthesis, materials science, and coupling reactions (such as the Suzuki reaction).
3. What should be noted when using it?
It should be stored in a sealed, light-proof, and dry environment; during operation, protective equipment (gloves, goggles) should be worn to avoid inhaling dust or coming into contact with the skin; it is irritating, so it should be handled in a fume hood and the waste should be disposed of in accordance with the regulations for hazardous chemicals.

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