3-Hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline
[CAS# 5423-67-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 3-Hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline
• Synonyms: 1,2,3,4-Tetrahydrobenzo[h]quinolin-3-ol
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• CAS Registry Number: 5423-67-6
• EC Number: 226-556-6
• SMILES: C1C(CNC2=C1C=CC3=CC=CC=C32)O

Properties

• Melting point: 148-150 °C (at 760 mmHg)
• Bointng point: 424.3 °C

Safety Data

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

Hazard Classification

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

Discovery and Applications

3-Hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline is a noteworthy compound recognized for its unique structure and wide range of applications. The compound has a molecular formula of C15H13NO and features a fused ring system consisting of a benzoquinoline skeleton and a hydroxyl group. Its unique structure endows it with important chemical and biological properties, making it valuable in various fields.

The discovery of 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline stems from the exploration of heterocyclic compounds, which are known for their diverse applications in medicinal chemistry and materials science. The structure of the compound includes a tetrahydrobenzoquinoline core and a hydroxyl group, which contributes to its chemical reactivity and biological activity. Researchers initially isolated and studied this compound to understand its potential in different chemical reactions and its possible therapeutic effects.

In medicinal chemistry, 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline has attracted much attention for its potential therapeutic applications. It is able to form various derivatives, thus becoming a useful intermediate for the synthesis of new drugs. The hydroxyl groups in the structure can participate in hydrogen bonding and other interactions that affect the biological activity of 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline-derived compounds. This property is particularly useful in designing drugs with specific interactions and higher efficacy.

The unique structure of this compound also makes it relevant to the field of organic synthesis. As an intermediate, 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline is used to make complex molecules and materials. Its versatility makes it useful in developing new materials with special properties, such as electronic devices or advanced coatings. The reactivity of the hydroxyl group helps it form new chemical bonds and structures.

In addition to its applications in medicine and organic synthesis, 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline has also attracted much attention in chemical research due to its potential role in studying reaction mechanisms and chemical properties. The compound is capable of a variety of chemical transformations, making it a valuable tool for exploring new reaction pathways and developing innovative chemical processes.

As with any chemical compound, safety considerations are important when working with 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline. Proper handling and usage guidelines must be followed to ensure safe laboratory practices and minimize potential risks.

References

2023. Multimodal action of KRP203 on phosphoinositide kinases in vitro and in cells. Biochemical and Biophysical Research Communications, 680.
DOI: 10.1016/j.bbrc.2023.08.050

2022. A quantitative high-throughput screen identifies compounds that lower expression of the SCA2-and ALS-associated gene ATXN2. The Journal of Biological Chemistry, 298(8).
DOI: 10.1016/j.jbc.2022.102228

2011. High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. Antiviral Research, 91(3).
DOI: 10.1016/j.antiviral.2011.06.006