5432-09-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloroquinolin-8-amine is used as a key intermediate in the synthesis of various bioactive compounds, contributing to the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Production:
5-CHLOROQUINOLIN-8-AMINE serves as an intermediate in the production of agrochemicals, playing a crucial role in the development of effective pesticides and other agricultural products.
Used in Dye Manufacturing:
5-Chloroquinolin-8-amine is utilized in the manufacturing of dyes, where its unique chemical properties contribute to the creation of vibrant and stable colorants for various applications.
Used in Specialty Chemicals Production:
5-CHLOROQUINOLIN-8-AMINE is also used as an intermediate in the production of specialty chemicals, which are essential for a wide range of industrial applications.
Used in Research and Development:
5-Chloroquinolin-8-amine is employed in scientific research and development, where its versatile reactivity and potential for chemical transformations are explored to create new materials and innovative solutions.

InChI:InChI=1/C9H7ClN2/c10-7-3-4-8(11)9-6(7)2-1-5-12-9/h1-5H,11H2

Upstream product

• 7647-01-0 hydrogenchloride 
• 607-35-2 8-nitroquinoline 
• 578-66-5 8-amino quinoline 
• 67-56-1 methanol 
• 6942-98-9 5-chloro-8-nitroquinoline 

Downstream Products

• 1020663-76-6 2-amino-N-(5-chloro-quinolin-8-yl)-benzenesulfonamide 

Relevant academic research and scientific papers

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature

The direct transformation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C-X bonds can be transformed into diverse C-O, C-S, C-C and C-N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C-H activation and the C-H activation step is involved in the rate-limiting step. An isolated Pd(ii) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(iv) to form a C-X bond was favored.