8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline
[CAS# 100331-89-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline
• Synonyms: 5-(2-bromoacetyl)-8-phenylmethoxy-1H-quinolin-2-one
• Molecular Formula: C₁₈H₁₄BrNO₃
• Molecular Weight: 372.21
• CAS Registry Number: 100331-89-3
• EC Number: 675-817-4
• SMILES: C1=CC=C(C=C1)COC2=C3C(=C(C=C2)C(=O)CBr)C=CC(=O)N3

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.685, Calc.^*
• Boiling Point: 596.4±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 314.5±28.7 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335-H341
• Precautionary Statements: P203-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-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.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline is a synthetic compound derived from the quinoline family, known for its broad utility in medicinal and organic chemistry. The discovery of this compound can be traced to research focused on modifying quinoline structures to develop molecules with potential biological activity, particularly for antimicrobial and anticancer purposes. Quinoline derivatives have long been recognized for their pharmacological properties, and the strategic addition of functional groups like benzyloxy and bromoacetyl enhances their reactivity and bioactivity.

The benzyloxy group at the 8-position serves as a protecting group for the hydroxyl moiety, making the molecule more amenable to specific synthetic modifications. This protection allows for selective reactions at other positions on the quinoline ring. The presence of the 2-hydroxy group introduces hydrogen bonding potential, which can influence the compound’s ability to interact with biological targets. Meanwhile, the bromoacetyl group at the 5-position imparts electrophilicity, enabling reactions such as nucleophilic substitution or facilitating the formation of heterocyclic rings through cyclization.

One significant application of 8-benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline is in the synthesis of more complex heterocyclic compounds. The bromoacetyl group is particularly useful for introducing additional functional groups or forming fused ring systems. This type of transformation is crucial in drug discovery, where the generation of structurally diverse molecules can lead to the identification of new therapeutics. For example, quinoline-based derivatives have shown promise as inhibitors of enzymes critical to bacterial and cancer cell proliferation.

Furthermore, 8-benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline is employed as an intermediate in the development of ligands for coordination chemistry. The hydroxyl and carbonyl functionalities enable this molecule to chelate metal ions effectively, making it valuable for creating metal-based complexes with potential applications in catalysis or medical imaging. Researchers exploring metal complexes of quinoline derivatives have demonstrated that such compounds can exhibit enhanced biological activity due to the metal’s role in facilitating interactions with biological targets.

Overall, the discovery and application of 8-benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline highlight its importance in synthetic chemistry and pharmaceutical research. The functional groups incorporated into this molecule allow for versatile transformations, contributing to advancements in the design of new drugs and materials.