2-Chloro-6-(2,6-Dichloro-3,5-Dimethoxyphenyl)quinazoline: Properties & Use
2-Chloro-6-(2,6-Dichloro-3,5-Dimethoxyphenyl)quinazoline: Properties & Use
2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline is a polychlorinated, methoxy-substituted quinazoline building block widely used in medicinal chemistry and drug discovery research as a versatile intermediate for the synthesis of biologically active heterocyclic compounds.
- Chemical Name
- 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline
- SKU / Catalog Number
- C174513
- Core Scaffold
- Quinazoline (bicyclic aromatic heterocycle containing two nitrogen atoms)
- Key Functional Groups
- C2-chloro (electrophilic handle), C6-aryl (2,6-dichloro-3,5-dimethoxyphenyl), two methoxy groups
- Primary Research Use
- Synthetic intermediate and building block in medicinal chemistry programs targeting kinase-related pathways
- Supplier
- Aladdin Scientific
Chemical Structure and Key Physicochemical Features
2-Chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline belongs to the quinazoline family of bicyclic aromatic heterocycles, characterized by a benzene ring fused to a pyrimidine ring. The compound carries three chlorine atoms in total: one at the C-2 position of the quinazoline ring and two at the 2,6-positions of the pendant phenyl group. Two methoxy substituents occupy the 3,5-positions of the same aryl ring, creating a sterically crowded and electronically modulated environment around the biaryl axis.
The C-2 chloro group on the quinazoline core is a highly reactive electrophilic site amenable to nucleophilic aromatic substitution (SNAr) and transition-metal-catalyzed cross-coupling reactions (e.g., Buchwald–Hartwig amination, Suzuki–Miyaura coupling). The ortho-dichloro substitution on the pendant phenyl ring introduces significant steric bulk and can influence the dihedral angle between the two aromatic planes, which is an important consideration for molecular recognition and binding affinity in drug design.
The methoxy groups contribute electron-donating resonance effects to the distal aryl ring while also providing additional hydrogen-bond-acceptor capacity, features that are frequently exploited when optimizing compounds for target binding and ADMET properties.
Role as a Synthetic Intermediate in Medicinal Chemistry
Quinazoline derivatives constitute one of the most clinically validated heterocyclic scaffolds in modern drug discovery. Numerous approved therapeutics—particularly kinase inhibitors used in oncology—are built upon the quinazoline core. The presence of a leaving group at C-2 makes 2-chloroquinazolines especially valuable as late-stage diversification handles, allowing rapid library synthesis via parallel coupling with amines, thiols, or organometallic partners.
In the specific case of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline, the pre-installed biaryl fragment at C-6 provides a differentiated pharmacophoric element compared with simpler 2-chloroquinazolines. The 2,6-dichloro-3,5-dimethoxyphenyl group mimics substitution patterns found in natural products and synthetic drug candidates that interact with ATP-binding pockets and other hydrophobic protein cavities. Researchers can exploit the reactive C-2 chloride to introduce diverse nitrogen- or oxygen-based nucleophiles, generating focused libraries of 2-substituted quinazoline analogs for biological screening.
The compound is therefore positioned primarily as a research-grade building block and intermediate, suitable for exploratory synthesis campaigns in academic and pharmaceutical research settings.
Handling, Storage, and Safety Considerations
As a polychlorinated aromatic compound, 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline should be handled with standard laboratory precautions appropriate for reactive heterocyclic intermediates. Personnel should wear appropriate personal protective equipment including chemical-resistant gloves, safety glasses, and a laboratory coat. Work should be carried out in a well-ventilated fume hood to minimize inhalation exposure to fine particulate or vapors.
The compound should be stored in a tightly sealed container, away from moisture and incompatible reagents such as strong bases, strong oxidizers, and reactive nucleophiles that could react with the C-2 chloride or the aromatic chlorines under forcing conditions. Storage at controlled room temperature or under refrigeration in a dry environment is generally recommended for long-term stability of chlorinated heterocyclic building blocks; researchers should consult the product-specific Certificate of Analysis (CoA) and Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative storage conditions and shelf-life guidance.
Waste disposal must comply with applicable local, national, and institutional regulations governing halogenated organic compounds.
Quality and Purity Specifications
Aladdin Scientific supplies 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (SKU: C174513) as a research-grade reagent. Purity and analytical characterization data are documented on the product-specific Certificate of Analysis (CoA), which customers are encouraged to download directly from the Aladdin Scientific website or request at the time of order.
Typical analytical methods used to characterize quinazoline building blocks of this type include high-performance liquid chromatography (HPLC) for purity determination, nuclear magnetic resonance (NMR) spectroscopy for structural confirmation, and mass spectrometry (MS) for molecular weight verification. Researchers requiring material for regulatory submissions or GMP-adjacent workflows should contact Aladdin Scientific's technical support team to discuss available documentation and custom purity requirements.
For procurement inquiries, bulk pricing, or custom synthesis services related to this compound, researchers and lab managers can contact Aladdin Scientific directly through the product page or customer service channels.
Frequently asked questions
What is the primary research application of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline?
This compound serves primarily as a synthetic building block and intermediate in medicinal chemistry, particularly for the construction of 2-substituted quinazoline analogs via nucleophilic substitution or transition-metal-catalyzed coupling at the reactive C-2 chloride position. It is relevant to drug discovery programs targeting kinase-related or other therapeutic pathways.
How should I store C174513 to ensure long-term stability?
Chlorinated heterocyclic building blocks of this type are generally best stored in a tightly sealed container in a cool, dry environment away from moisture and incompatible reagents. Please refer to the product-specific Safety Data Sheet (SDS) and Certificate of Analysis (CoA) available from Aladdin Scientific for authoritative storage and shelf-life recommendations.
What reactions can be performed at the C-2 chloro position of this quinazoline?
The C-2 chloro group is an activated electrophilic site well-suited for nucleophilic aromatic substitution (SNAr) with amines, alcohols, and thiols, as well as transition-metal-catalyzed cross-coupling reactions such as Buchwald–Hartwig amination and Suzuki–Miyaura coupling. These transformations enable rapid diversification of the quinazoline scaffold for structure–activity relationship studies.
Is a Certificate of Analysis available for SKU C174513?
Yes. Aladdin Scientific provides a Certificate of Analysis (CoA) for C174513 documenting purity and characterization data. Customers can download the CoA from the product page on the Aladdin Scientific website or request it through customer service at the time of ordering.
References
- Comprehensive reference on quinazoline chemistry and biological activity as a class — textbook-level knowledge; no specific paper cited.
- Aladdin Scientific product page for C174513: 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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