3-Bromo-4-methylquinoline cas 59280-69-2 support custom synthesis

Physical and chemical properties

· Appearance: Usually white to off-white or light yellow crystalline powder or solid.
· Melting point: The reported melting points in the literature are typically around 80-84°C.
· Solubility: Easily soluble in organic solvents such as dichloromethane, chloroform, ethyl acetate, N,N-dimethylformamide, tetrahydrofuran, etc. The solubility in water is very low.
· Chemical properties:
· Reactivity of bromine atom: The bromine atom at the 3-position is an important reaction site. Due to the influence of the adjacent nitrogen atom and the aromatic ring, it is a relatively active aryl bromide and can participate in various cross-coupling reactions, such as Suzuki coupling, Buchwald-Hartwig amination, etc. This makes it a key building block for constructing more complex molecules.
· Basicity of nitrogen atom: The nitrogen atom on the quinoline ring has basicity and can form salts with acids or act as a ligand to coordinate with metals.
· Reactivity of methyl group: The methyl group at the 4-position has a certain acidity and can form a carbon anion under the action of strong bases (such as LDA), thereby reacting with electrophilic reagents to achieve functional group transformation.
Main purpose

3-Bromo-4-methylquinoline is almost exclusively used as an organic synthesis intermediate in the field of chemistry, especially in the research and development of medicine and materials science.
1. Medicinal Chemistry:
· The quinoline structure is the core pharmacophore of many drug molecules, possessing various biological activities such as antibacterial, antimalarial, and anti-tumor properties.
· Through reactions like Suzuki coupling, 3-bromo-4-methylquinoline can be linked with various arylboronic acids to construct a diverse library of quinoline-based compounds, which can be used for screening new drug candidate molecules.
· Through Buchwald-Hartwig coupling, an amino group can be introduced at the 3rd position, which is a common structural unit in the construction of kinase inhibitors and other targeted drugs.
2. Materials Chemistry:
· Quinoline derivatives can be used to synthesize functional materials such as organic light-emitting diodes and fluorescent probes. By modifying their 3rd and 4th positions, the photophysical properties of the molecules can be finely controlled.
Synthesis method
The common synthetic routes usually start with readily available quinoline derivatives as the initial raw materials:
· Starting from 4-methylquinoline: 4-methylquinoline can be prepared by the Skraup synthesis method or other quinoline synthesis methods. Then, in an acetate or other solvent, it undergoes an electrophilic bromination reaction with bromine or N-bromobutyldicarbonate. Due to the activation effect of the 4-methyl group, the bromination selectively occurs at the adjacent position (i.e., the 3-position), thereby efficiently obtaining the target product.
Safety and Storage
· Hazard: The currently available toxicity data may be incomplete. As an organic compound, it should be avoided to inhale its dust and to prevent contact with eyes and skin.
· Procedure: It is recommended to operate in a well-ventilated chemical fume hood and wear appropriate personal protective equipment, such as protective glasses, gloves and laboratory coat.
· Storage: It should be stored in a sealed manner in a cool, dry and dark place. Generally, it is recommended to store it in a refrigerator at 2-8°C.