5-bromo-1-cyclopropyl-4-fluoro-1H-indazole

Name: 5-bromo-1-cyclopropyl-4-fluoro-1H-indazole
Other Names: 5-bromo-1-cyclopropyl-4-fluoroindazole
CAS Number: 2490501-34-1
Chemical Formula: C₁₀H₈BrFN₂
Molecular Weight: 255.09
Density: 1.835±0.14 g/cm³ (25°C, predicted value)
Boiling Point: 344.781±22.00 °C (760 Torr, predicted value)
Storage Conditions: Store in a sealed container at room temperature in a dry place.
Sensitivity: Sensitive to light and moisture (protect from light recommended).
Appearance: Solid (white to off-white powder or crystals).
Specific Gravity: 1.835 (Predicted Value)
Color: White to pale yellow
Risk Terms: R22 (Harmful if ingested), R41 (Serious eye irritation) (Refer to similar structures)
Safety Terms: S26 (If contact with eyes occurs, rinse immediately with plenty of water and consult a doctor), S39 (Wear goggles or a face mask)
Customs Code: 2933990090 (Refer to similar indazole compounds)

Properties:
Physical Properties: This compound is a fluorine- and bromine-substituted indazole heterocyclic compound, a solid. Due to the presence of bromine and fluorine atoms in the molecule, it has a high density (approximately 1.835 g/cm³). Indazole compounds are generally basic and can combine with acidic substances to form salts.

Chemical Properties: Containing reactive bromine substituents, it can undergo coupling reactions (such as Suzuki, Heck, Negishi, etc.), making it a good substrate for cross-coupling reactions. The introduction of cyclopropyl and fluorine atoms can regulate the electronic properties and lipid solubility of the molecule. This compound is relatively stable at room temperature and pressure, but contact with strong oxidizing agents, strong acids, and strong bases should be avoided.

Uses:
Pharmaceutical intermediate: As an important pharmaceutical and chemical intermediate, it is used to synthesize biologically active indazole compounds, especially kinase inhibitors and antitumor drugs.

Organic synthesis building block: In medicinal chemistry and pesticide chemistry, it serves as a key intermediate for constructing complex nitrogen-containing heterocyclic skeletons.

Research and development uses: Primarily used in organic synthesis during laboratory research and development and chemical production processes.

Preparation

This compound can be synthesized via the following route (refer to similar methods for the synthesis of indazole compounds):

Starting material: 2-bromo-3-cyclopropyl-6-fluorobenzaldehyde

Cyclization reaction: Reaction with hydrazine hydrate in ethylene glycol, first stirred at 90°C for 2 hours, then heated to 150°C for 16 hours.

Post-treatment: After cooling, extraction with ice-cold water and ethyl acetate, washing the organic layer with water and brine, drying with anhydrous sodium sulfate, and concentrating under vacuum.

Purification: Purification by silica gel column chromatography (0-20% ethyl acetate/hexane), further purification by reversed-phase preparative liquid chromatography if necessary.

Safety Information

Hazards: This compound belongs to halogen-containing heterocyclic compounds and may be irritating. Ingestion may be harmful and may cause serious eye damage.

Precautions: Handle in a fume hood, wearing protective gloves, goggles, and a lab coat. Avoid inhaling dust and avoid contact with skin and eyes.

Storage: Store in a sealed container in a dry, cool place, away from light and moisture.

Waste Disposal: Dispose of contents/containers in accordance with local/regional/national/international regulations. Do not discard indiscriminately.

First Aid Measures:
Inhalation: Move the patient to fresh air. If breathing is difficult, administer oxygen and seek medical attention.

Skin Contact: Wash immediately with plenty of soap and water.

Eye Contact: Rinse immediately with plenty of water for at least 15 minutes. Seek medical attention.

Ingestion: Rinse mouth and seek immediate medical attention.