4-Chloro-6-quinazolinol
[CAS# 848438-50-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 4-Chloro-6-quinazolinol
• Synonyms: 4-Chloroquinazolin-6-ol
• Molecular Formula: C₈H₅ClN₂O
• Molecular Weight: 180.59
• CAS Registry Number: 848438-50-6
• EC Number: 823-477-4
• SMILES: C1=CC2=C(C=C1O)C(=NC=N2)Cl

Properties

• Solubility: Very slightly soluble (0.38 g/L) (25 °C), Calc.^*
• Density: 1.500±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.71, Calc.^*
• Boiling Point: 333.0±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 155.2±22.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

4-Chloro-6-quinazolinol is a chemical compound with the molecular formula C8H6ClN3O. It consists of a quinazoline ring, which is a heterocyclic structure composed of a benzene ring fused to a pyrimidine ring, with a chloro group attached to the 4-position and a hydroxyl group at the 6-position of the quinazoline ring.

The discovery of 4-chloro-6-quinazolinol can be traced back to the study of quinazoline derivatives, a class of compounds with diverse biological and chemical properties. Quinazoline and its derivatives have been well-known in organic chemistry due to their potential in medicinal chemistry. The quinazoline core structure is widely found in various bioactive compounds, including those with anticancer, anti-inflammatory, and antimicrobial properties. Researchers have been exploring various substitutions on the quinazoline ring to modify its biological activity, and 4-chloro-6-quinazolinol is one such derivative.

In terms of applications, 4-chloro-6-quinazolinol is primarily utilized in the field of medicinal chemistry. It has been investigated for its potential biological activity, particularly its role as an intermediate in the synthesis of other quinazoline-based compounds with therapeutic properties. Quinazoline derivatives, including 4-chloro-6-quinazolinol, have been of interest for their potential to act as kinase inhibitors, with implications in cancer therapy. Kinase inhibitors are compounds that can modulate the activity of kinases, enzymes that play a crucial role in regulating cellular processes, including growth and metabolism. In particular, quinazoline-based kinase inhibitors have been studied for their potential in the treatment of various cancers.

Furthermore, 4-chloro-6-quinazolinol has been explored for its possible antimicrobial properties. Quinazoline derivatives, including this compound, have been shown to exhibit activity against a range of microorganisms, and as such, they have been studied as potential candidates for the development of new antibiotics or other antimicrobial agents. The presence of both the chloro and hydroxyl groups in the structure of 4-chloro-6-quinazolinol may contribute to its interaction with biological targets, enhancing its potential activity in medicinal applications.

In addition to medicinal chemistry, 4-chloro-6-quinazolinol may also find applications in other areas, including organic synthesis. Its structure makes it a useful building block in the preparation of more complex molecules, particularly those in the quinazoline family. These derivatives have been synthesized for various studies in drug discovery, where modifications to the quinazoline core are commonly explored to enhance potency, selectivity, and pharmacokinetic properties of potential drug candidates.

Overall, while 4-chloro-6-quinazolinol has not gained significant prominence in clinical applications, it remains an important compound in the realm of synthetic organic chemistry and drug discovery. Its derivatives continue to be explored for their biological activities, particularly in the development of kinase inhibitors and antimicrobial agents, with ongoing research into their potential therapeutic applications.

References

Lee, J.W. et al. (2022). Structure-activity relationships of novel quinazoline derivatives with high selectivity for HER2 over EGFR. Archives of Pharmacal Research, 45(3), 123-141.
DOI: https://doi.org/10.1007/s12272-022-01376-4

Sun Pharmaceutical Industries Ltd (2021). Pyrrolidine and piperidine compounds. WO-2021090245-A1, 2021-05-14.