4-Isoquinolylamine
[CAS# 23687-25-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Isoquinoline compound
• Name: 4-Isoquinolylamine
• Synonyms: 4-Aminoisoquinoline; Isoquinolin-4-ylamine
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17
• CAS Registry Number: 23687-25-4
• EC Number: 245-823-8
• SMILES: C1=CC=C2C(=C1)C=NC=C2N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 107-113 °C (Expl.)
• Index of Refraction: 1.708, Calc.^*
• Boiling Point: 360.0±17.0 °C (760 mmHg), Calc.^*
• Flash Point: 198.9±8.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Isoquinolylamine is an organic compound that features an isoquinoline ring structure, a nitrogen-containing heterocycle, attached to an amine group at the 4-position. The molecular formula for 4-isoquinolylamine is C9H10N2, and it is characterized by its distinct heterocyclic structure that combines a benzene ring fused to a pyridine ring. This compound belongs to the family of isoquinoline derivatives, which are known for their biological activity and chemical versatility.

The discovery of 4-isoquinolylamine is part of the broader exploration of isoquinoline derivatives, which has been an area of significant interest in medicinal chemistry and synthetic organic chemistry. The presence of the nitrogen atom in the isoquinoline ring imparts unique reactivity, which can be exploited for a variety of chemical transformations. The synthesis of 4-isoquinolylamine typically involves the reduction of isoquinoline or the direct amination of isoquinoline derivatives. Advanced synthetic techniques often include catalytic methods or electrophilic aromatic substitution to introduce the amine group into the isoquinoline ring.

One of the key applications of 4-isoquinolylamine is its role as an intermediate in the synthesis of bioactive molecules, especially those with potential medicinal properties. Isoquinoline derivatives have been found to exhibit a wide range of biological activities, such as anticancer, antibacterial, and antifungal properties. The amine functionality at the 4-position enhances the ability of 4-isoquinolylamine to serve as a building block for the design of novel therapeutic agents. For example, derivatives of 4-isoquinolylamine have been investigated for their role in the development of inhibitors for specific enzymes involved in cancer progression or infectious diseases.

In particular, isoquinoline-based compounds are known for their interactions with enzymes such as protein kinases, which are involved in regulating cellular functions like growth and survival. This has led to the development of 4-isoquinolylamine derivatives as potential kinase inhibitors. Furthermore, due to the lipophilic nature of the isoquinoline ring, these compounds are often able to cross biological membranes and interact with intracellular targets, making them useful in drug discovery efforts.

Additionally, 4-isoquinolylamine has been explored in the synthesis of fluorescent probes and sensors for biological applications. The unique electronic properties of the isoquinoline structure, combined with the amine group, allow the development of compounds with selective binding affinity for certain biological molecules or metal ions. These probes are valuable in imaging and diagnostic applications, where the detection of specific biomolecules is required.

In material science, derivatives of 4-isoquinolylamine have been investigated for their potential use in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic semiconductors. The ability to functionalize the isoquinoline core allows for the design of molecules with desirable electronic properties, which can be tuned for specific applications in the electronics industry.

4-Isoquinolylamine is also of interest in the field of coordination chemistry, where it can act as a ligand to form complexes with transition metals. These metal complexes are often studied for their catalytic properties and potential in applications such as hydrogenation, oxidation, and other important chemical transformations.

In conclusion, 4-isoquinolylamine is a versatile and valuable compound in the fields of medicinal chemistry, material science, and chemical synthesis. Its role as a building block for the development of bioactive molecules, fluorescent probes, and electronic materials highlights its potential in various advanced applications. As research progresses, the discovery of new derivatives and applications of 4-isoquinolylamine is expected to provide further insights into its broad utility in both scientific and industrial fields.

References

2007. Mechanistic Study on Rearrangement Cascades Starting from Annulated 2‐Aza‐hepta‐2,4‐dienyl‐6‐ynyl Anions: Formation of Aniline and Azepine Derivatives. *Chemistry (Weinheim an der Bergstrasse, Germany)*, 13(9).
DOI: 10.1002/chem.200601491

2003. Novel High Energy Intermediate Analogues with Triazasterol-Related Structures as Potential Inhibitors of the Ergosterol Biosynthesis II. Optimization of the Synthesis of 1,6,7,11b-Tetrahydro-2H-pyrimido[4,3-a]isoquinolin-4-amines as Parent Compounds of Novel 8,13,15-Triazasteroids. *Monatshefte für Chemie / Chemical Monthly*, 134(5).
DOI: 10.1007/s00706-002-0559-7

1956. A. R. Osborn, K. Schofield, and L. N. Short. J. Chem. Soc. 4191.
URL: Not available