CAS Number 1442437-21-9 (Main); 1823277-97-9 (Backup)
Chemical Formula: C₅H₄N₂O₄
Molecular Weight: 156.1
InChI: InChI=1S/C₅H₄N₂O₄/c8-2-1-3(9)6-7-4(2)5(10)11/h1H,(H,10,11)(H₂,6,8,9)
InChIKey: XCNDXNJULVWJCE-UHFFFAOYSA-N
SMILES: C1=C(C(=NNC1=O)C(=O)O)O
Density: 1.88±0.1 g/cm³ (Predicted)
Water Solubility: Soluble in water, DMSO and other polar solvents
Storage Conditions: Store in a sealed, dry place at room temperature or 2–8°C protected from light
Sensitivity: Sensitive to moisture
Appearance: Solid powder
Specific gravity: 1.88±0.1 g/cm³
Color: White to off-white
MDL Number: MFCD30489098 / MFCD31652377
Hazard Symbol: Xi (Irritant)
Risk Terms: H315 (Causes skin irritation); H319 (Causes serious eye irritation); H335 (Causes respiratory irritation)
Safety Terms: P264 (Clean skin thoroughly after handling); P280 (Wear protective gloves/eyes/face shield); P305+P351+P338 (If in eyes: Rinse carefully with water for several minutes); P403+P233 (Store in a well-ventilated place, keep container tightly closed)
Customs Number 2933.99 (Other Nitrogen-Containing Heterocyclic Compounds)
I. Properties
4,6-Dihydroxypyridazine-3-carboxylic acid belongs to the pyridazine class of nitrogen-containing heterocyclic compounds. The molecule contains two hydroxyl groups (or the keto-enol tautomer form: 4-hydroxy-6-oxo-1,6-dihydropyridazine-3-carboxylic acid) and one carboxylic acid group. This compound exhibits strong polarity, containing multiple hydrogen bond donors and acceptors, and can participate in various organic synthesis reactions such as esterification, amidation, and condensation. It is distinctly acidic (pKa prediction value is approximately -3.17±0.40), readily forming salts under alkaline conditions and precipitating freely under acidic conditions. Due to the electron-deficient nature of the pyridazine ring, this compound exhibits unique reactivity in electrophilic substitution reactions and is an important module for constructing complex heterocyclic molecular skeletons.
II. Uses
This product is mainly used as an organic synthesis intermediate and a pharmaceutical chemical intermediate, and has significant value in laboratory research and development and pharmaceutical production. Its core applications include:
* **Drug Impurity Reference Standards:** Serving as Impurity 9 and Related Compound 4 for Declavatitinib (development code BMS-986165) in quality control, analytical method development, and method validation (AMV).
* **Heterocyclic Synthesis Building Blocks:** Used to synthesize more complex pyridazines, pyrazines, and other fused heterocyclic compounds, serving as key intermediates in innovative drug development.
* **Biochemical Research:** Used as structural fragments in pharmaceutical and biochemical research to explore potential biological activities and enzyme inhibitory activities (such as oxidoreductases). III. Preparation Methods Currently, the main industrial and laboratory route for preparing this compound is the ester hydrolysis method:
Main Synthetic Route: Using ethyl 4,6-dihydroxypyridazine-3-carboxylate (CAS: 1352925-63-3) as the starting material, the ester group is hydrolyzed under reflux in an alkaline aqueous solution (such as a sodium hydroxide/ethanol-water system). After the reaction is complete, the mixture is cooled and acidified with dilute hydrochloric acid to pH 1–2, causing the product to precipitate out. The product is then filtered, washed, dried, and recrystallized (using water or an ethanol-water mixture) to obtain the high-purity target product.
Other potential routes include hydroxylation of pyridazine-3-carboxylic acid derivatives or hydrolysis/oxidation of 4,6-dichloropyridazine-3-carboxylic acid. However, the ester hydrolysis method is widely used due to its short route, mild conditions, and stable yield.
IV. Safety Information
GHS Hazard Categories: Skin irritation/irritation (Category 2); Serious eye damage/irritation (Category 2A); Specific target organ toxicity—single exposure, respiratory irritation (Category 3)
Pictogram: Exclamation mark
Signal Word: Warning
Main Hazards: Harmful if swallowed (H302); Causes skin irritation (H315); Causes serious eye irritation (H319); May cause respiratory irritation (H335)
Personal Protection: Wear protective gloves (nitrile or neoprene), chemical safety goggles, respirator, or dust mask when handling; work in a fume hood or well-ventilated area.
First Aid Measures: Skin contact: Immediately wash with plenty of soap and water; Eye contact: Rinse with running water or saline solution for at least 15 minutes and seek medical attention; Inhalation: Move to fresh air and perform artificial respiration if necessary; Ingestion: Rinse mouth and seek immediate medical attention.
Fire Control Measures: Use dry powder, carbon dioxide, or sand to extinguish the fire. Avoid using direct water flow.
Spill Handling Collect the leaked material in a sealed container and absorb the residue with an inert absorbent material (such as sand or vermiculite) to prevent it from entering the sewer system.
Disposal: Treat as hazardous waste according to local regulations and dispose of it by a qualified waste management company.
Storage Requirements: Store in a sealed container in a dry, cool, and well-ventilated place, away from oxidants, strong acids, strong alkalis, and food containers.
V. Our Production Advantages and Capacity
Production Advantages:
High Purity Guarantee: Our company uses an optimized ester hydrolysis process, achieving a product purity of ≥98% (HPLC), meeting the stringent requirements for drug impurity reference standards.
Comprehensive Quality System: The production process is certified by ISO 9001 quality management system. Each batch provides a complete COA analysis report (including HPLC purity, NMR structure confirmation, MS molecular weight verification, moisture content, residual solvents, etc.).
Professional Impurity Reference Standard Supply: As a professional manufacturer of Deucravacitinib impurity 9, our company possesses mature process routes and stable quality standards. Our products can be used for quality control in ANDA applications and commercial production.
Flexible customization capabilities: Supports customized synthesis from gram-level to ten-kilogram-level.
Rapid response and stable supply: Standard specifications are kept in stock, enabling delivery within 2-3 business days; customized projects are assigned a dedicated project manager to ensure on-time delivery and quality.
Post time: May-18-2026
