4-Chloro-1,2-dihydropyridazine-3,6-dione: Properties & Applications
4-Chloro-1,2-dihydropyridazine-3,6-dione: Properties & Applications
4-Chloro-1,2-dihydropyridazine-3,6-dione is a chlorinated dihydropyridazinedione heterocycle widely used as a reactive building block in medicinal chemistry and synthetic organic research.
- IUPAC Name
- 4-chloro-1,2-dihydropyridazine-3,6-dione
- Core Scaffold
- Dihydropyridazine-3,6-dione (pyridazinedione)
- Key Functional Group
- C-4 chloro substituent enabling nucleophilic aromatic substitution
- Primary Research Use
- Synthetic intermediate and heterocyclic building block for drug discovery
- SKU
- C193825
- Supplier
- Aladdin Scientific
Chemical Structure and Key Properties
4-Chloro-1,2-dihydropyridazine-3,6-dione belongs to the pyridazinedione family of nitrogen-containing heterocycles. Its core structure features a six-membered ring containing two adjacent nitrogen atoms, two carbonyl groups at the 3- and 6-positions, and a chlorine substituent at the 4-position. This arrangement confers significant electrophilic character at C-4, making the compound a valuable substrate for nucleophilic aromatic substitution (SNAr) reactions.
The presence of dual lactam-type NH groups in the dihydro form provides additional sites for N-alkylation or N-acylation, further broadening its synthetic utility. The compound is typically handled as a stable crystalline solid under standard laboratory storage conditions, away from moisture and strong bases.
Synthesis and Reactivity
Dihydropyridazine-3,6-dione derivatives are classically accessible from maleic hydrazide or related diazine precursors through halogenation reactions. Introduction of a chlorine atom at the 4-position significantly activates the ring toward displacement by a variety of nucleophiles including amines, thiols, and alkoxides under mild to moderate reaction conditions.
Because the chloro group is activated by the electron-withdrawing carbonyl groups flanking the ring, SNAr proceeds efficiently with primary and secondary amines, enabling rapid library synthesis of diversely substituted pyridazinedione analogs. This reactivity profile makes 4-Chloro-1,2-dihydropyridazine-3,6-dione a versatile electrophilic partner in multi-step synthetic sequences.
Applications in Drug Discovery and Medicinal Chemistry
The pyridazinedione scaffold is recognized in medicinal chemistry for its ability to mimic bioactive conformations and engage in hydrogen-bonding interactions with biological targets. 4-Chloro-1,2-dihydropyridazine-3,6-dione serves as a privileged starting material for the preparation of pharmacologically relevant compounds, including potential kinase inhibitors, antimicrobial agents, and other bioactive small molecules.
Researchers employ this compound in fragment-based drug discovery (FBDD) and high-throughput synthesis workflows, exploiting the SNAr handle to introduce structural diversity at the 4-position while retaining the hydrogen-bond donor/acceptor features of the intact dione ring. Its compact molecular framework allows efficient exploration of chemical space within drug-like property ranges.
Handling, Storage, and Safety Considerations
As with all fine chemical reagents, 4-Chloro-1,2-dihydropyridazine-3,6-dione should be handled with appropriate personal protective equipment, including nitrile gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation exposure to dust or aerosols.
The compound should be stored in a tightly sealed container in a cool, dry environment, protected from light, moisture, and incompatible materials such as strong oxidizers and strong bases. Users are advised to consult the current Safety Data Sheet (SDS) available from Aladdin Scientific before use to obtain up-to-date hazard, handling, and disposal information specific to this material.
Frequently asked questions
What makes 4-Chloro-1,2-dihydropyridazine-3,6-dione useful as a synthetic building block?
The compound's chloro substituent at C-4 is activated by adjacent carbonyl groups, enabling efficient nucleophilic aromatic substitution with amines, thiols, and other nucleophiles. Combined with the N–H sites available for alkylation, this gives chemists multiple handles for diversification in a single compact scaffold.
How should 4-Chloro-1,2-dihydropyridazine-3,6-dione be stored to maintain its integrity?
The compound should be stored in a tightly sealed container under cool, dry conditions, away from light, moisture, strong oxidizers, and strong bases. Always consult the current SDS from Aladdin Scientific for specific storage temperature recommendations and hazard information.
In what research areas is the pyridazinedione scaffold most commonly encountered?
Pyridazinedione-containing compounds appear across medicinal chemistry, agrochemical research, and materials science. In drug discovery, the scaffold is valued for its hydrogen-bonding capacity, metabolic stability, and ability to serve as a bioisostere for other carbonyl-containing ring systems. 4-Chloro-1,2-dihydropyridazine-3,6-dione provides direct access to this privileged class.
What is the Aladdin Scientific SKU for 4-Chloro-1,2-dihydropyridazine-3,6-dione?
4-Chloro-1,2-dihydropyridazine-3,6-dione is listed under SKU C193825 in the Aladdin Scientific catalog. Contact your local Aladdin representative or visit the product page for current pricing, pack sizes, and purity specifications.
References
- Comprehensive Heterocyclic Chemistry III, Katritzky, A. R. et al. (Eds.), Elsevier, 2008. Chapter on pyridazines and their derivatives.
- Maleic hydrazide and pyridazinedione chemistry: a review of synthetic methods and biological activity. General reference — specific journal citation not available.
- Aladdin Scientific product catalog entry: 4-Chloro-1,2-dihydropyridazine-3,6-dione, SKU C193825.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）