Overview
6,7-Dimethoxyquinazolin-4-one is a heterocyclic organic compound belonging to the quinazolinone class. It serves as a critical building block in medicinal chemistry, particularly for synthesizing bioactive molecules targeting cardiovascular diseases and cancer. The dimethoxy substitution at the 6 and 7 positions enhances its electron-donating properties, making it valuable for designing kinase inhibitors. Industrial production typically involves cyclization of anthranilic acid derivatives or condensation reactions with amidines. Its high reactivity at the 4-position allows for further functionalization, enabling diverse pharmaceutical applications.
Physical and Chemical Properties
This compound exhibits moderate thermal stability with decomposition observed near 280°C. Its crystalline structure contributes to relatively low solubility in polar solvents like water, while organic solvents such as dimethyl sulfoxide (DMSO) dissolve it effectively. The electron-rich quinazolinone core participates in electrophilic substitution reactions. Spectroscopic characterization includes distinctive peaks in NMR (e.g., methoxy protons at ~3.9 ppm) and IR (C=O stretch at ~1680 cm⁻¹). The molecular weight of 206.20 g/mol falls within the typical range for drug intermediates, facilitating pharmacokinetic optimization in final APIs.
Main Applications
Approximately 70% of global production supplies the synthesis of alpha-1 adrenergic receptor antagonists like prazosin, used to treat hypertension. Recent applications focus on tyrosine kinase inhibitors (TKIs) for oncology, where the scaffold acts as a ATP-binding site competitor. Emerging uses include covalent inhibitor development through C4-position modifications. Some agrochemical formulations incorporate derivatives as growth regulators. The compound's versatility stems from its balanced lipophilicity (LogP ~1.5) and hydrogen bonding capacity.
Safety and Storage
As a fine chemical, proper handling requires nitrile gloves, protective eyewear, and fume hoods to prevent particulate inhalation. Although not classified as acutely toxic, prolonged exposure may cause irritation. Spills should be contained with inert absorbents like vermiculite. Long-term storage demands moisture-proof containers (preferably amber glass) under nitrogen atmosphere. Stability studies indicate ≤2% degradation over 24 months when stored at 2-8°C. Incompatibilities include strong oxidizers and acids, which may induce exothermic decomposition.
B2B Procurement Guide
Pharmaceutical-grade material should meet ICH Q7 standards with documented impurity profiles (e.g., heavy metals <10 ppm). Batch-specific HPLC chromatograms (typically C18 column, 254 nm detection) must accompany shipments. Reliable suppliers often provide process validation data and DMF access. For pilot-scale quantities (5-50 kg), lead times average 4-6 weeks. Consider auditing manufacturers for ISO 9001 certification and solvent recovery systems. Spot prices fluctuate with raw material (e.g., guaiacol) availability, with contract manufacturing offering 15-20% cost advantages for multi-ton orders.
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