23981-25-1

Basic information

• Product Name: 8-CHLORO-2-HYDROXYQUINOLINE
• Synonyms: 8-CHLORO-2-HYDROXYQUINOLINE;8-Chloroquinolin-2-ol;8-Chloro-2-hydroxy e;6-cloroquinolin-2(1H)-one;8-Chloro-2-hydroxyquinoline 97%;8-chloro-1H-quinolin-2-one;8-Chloro-2(1H)-Quinolinone
• CAS NO: 23981-25-1
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 23981-25-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 209-212 °C(lit.)
• Boiling Point: 373.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.339±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.70±0.70(Predicted)
• CAS DataBase Reference: 8-CHLORO-2-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO-2-HYDROXYQUINOLINE(23981-25-1)
• EPA Substance Registry System: 8-CHLORO-2-HYDROXYQUINOLINE(23981-25-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 23981-25-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Chloro-2-hydroxyquinoline is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
8-Chloro-2-hydroxyquinoline is used as a building block in the synthesis of complex organic molecules. It can be further modified and combined with other chemical groups to create a wide range of compounds with diverse properties and applications.
Used in Research and Development:
8-Chloro-2-hydroxyquinoline serves as a valuable research tool in the field of organic chemistry. It is used to study the properties and reactivity of quinoline derivatives, which can lead to the discovery of new compounds with potential applications in various industries.
Specific Applications:
8-Chloro-2-hydroxyquinoline is used to synthesize 8-chloro-2-(2-oxo-2-phenylethoxy)quinoline and 8-chloro-2-(2-oxopropoxy)quinolone. These synthesized compounds may have specific applications in various fields, such as pharmaceuticals, materials science, or chemical research.

Upstream product

• 73108-79-9 N-(2-chlorophenyl)-3-phenylacrylamide 
• 95-51-2 o-chloroaniline 
• 105703-65-9 (2E)-N-(2-chlorophenyl)cinnamamide 

Downstream Products

• 891842-52-7 2-bromo-8-chloro-quinoline 

Relevant articles and documents

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines

A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.

NITROGEN HETEROCYCLIC COMPOUNDS USEFUL AS PDE10 INHIBITORS

Unsaturated nitrogen heterocyclic compounds of formula (I): (I), as defined in the specification, compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, Huntington's Disease, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

Antimicrobial quinolones, their compositions and uses

This invention relates to novel antimicrobial compounds of formula; wherein X, R1, R3, R5, R6, and R8 are defined in the claims, and to their optical isomers, diastereomers or enantiomers, as well as pharmaceutically-acceptable salts, hydrates, and biohydrolyzable esters, amides and imides thereof, and to compositions and uses of such compounds. The invention also relates to compounds derived from these compounds having antimicrobial uses.