6-Bromo-5-methyl-2-pyridinamine
[CAS# 89466-17-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 6-Bromo-5-methyl-2-pyridinamine
• Molecular Formula: C₆H₇BrN₂
• Molecular Weight: 187.04
• CAS Registry Number: 89466-17-1
• EC Number: 873-233-6
• SMILES: CC1=C(N=C(C=C1)N)Br

Properties

• Solubility: Slightly soluble (5.4 g/L) (25 ºC), Calc.^*
• Density: 1.593±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 96-98 ºC^**
• Boiling point: 287.3±35.0 ºC (760 Torr), Calc.^*
• Flash point: 127.6±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Harris, Anthony R.; Tetrahedron 2011, V67(47), P9063-9066.

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

6-Bromo-5-methyl-2-pyridinamine is a chemical compound characterized by its distinctive pyridine ring with bromo and methyl substitutions, making it notable in both synthetic and medicinal chemistry. The compound's unique structure provides a basis for various applications, particularly in the synthesis of pharmaceuticals and in the development of new chemical entities.

The synthesis of 6-Bromo-5-methyl-2-pyridinamine involves the bromination of 5-methyl-2-pyridinamine, where bromine is introduced at the 6-position of the pyridine ring. This transformation typically requires careful control of reaction conditions to ensure selective bromination and to avoid unwanted side reactions. The method employed usually involves the use of brominating agents in the presence of appropriate solvents and catalysts. The reaction's success relies on optimizing conditions to achieve high yield and purity of the target compound.

The discovery of 6-Bromo-5-methyl-2-pyridinamine underscores advancements in organic chemistry, particularly in the manipulation of heterocyclic compounds. Pyridine derivatives are known for their versatility and reactivity, making them valuable in various chemical transformations. The introduction of bromine and methyl groups into the pyridine ring enhances its chemical properties, such as reactivity and selectivity in further reactions.

In medicinal chemistry, 6-Bromo-5-methyl-2-pyridinamine serves as an important intermediate in the synthesis of biologically active compounds. The bromine atom provides a site for nucleophilic substitution reactions, enabling the introduction of diverse functional groups. This property is exploited to create a range of derivatives with potential therapeutic applications. For instance, modifications to the pyridine ring can lead to compounds with specific biological activities, such as antimicrobial, anticancer, or anti-inflammatory effects.

The compound is also utilized in the development of pharmaceuticals where the pyridine ring's electronic and steric properties play a crucial role in the design of new drugs. By altering the substitution pattern on the pyridine ring, researchers can tailor the pharmacokinetic and pharmacodynamic properties of the resulting compounds. This approach facilitates the creation of more effective and selective drugs.

In addition to its pharmaceutical applications, 6-Bromo-5-methyl-2-pyridinamine finds use in materials science and organic synthesis. The bromine atom in the structure allows for further functionalization, which is valuable in the preparation of novel materials with unique properties. These materials can be employed in various fields, including electronics, catalysis, and sensor technology.

Overall, 6-Bromo-5-methyl-2-pyridinamine exemplifies the importance of structural modifications in heterocyclic chemistry. Its synthesis and applications highlight the compound's role as a versatile building block in both drug development and materials science. By leveraging its reactivity and functionalization potential, researchers can explore new chemical spaces and develop innovative solutions across multiple domains.