4-Chloro-5-fluoroindole: Properties, Uses & FAQs

4-Chloro-5-fluoroindole is a halogen-substituted indole building block widely used in medicinal chemistry and heterocyclic synthesis.

CAS Number

Not specified in source material — see product page for confirmed CAS

Molecular Formula

C8H5ClFN

Substitution Pattern

Chloro at position 4, fluoro at position 5 of the indole ring

Compound Class

Halogenated indole; bicyclic heteroaromatic

Primary Application

Synthetic building block for pharmaceutical and agrochemical research

Aladdin SKU

C191469

What Is 4-Chloro-5-fluoroindole?

4-Chloro-5-fluoroindole is a bicyclic heteroaromatic compound belonging to the indole family. The parent indole scaffold consists of a benzene ring fused to a pyrrole ring; in this derivative, a chlorine atom is installed at the 4-position and a fluorine atom at the 5-position of the benzene ring. These halogen substituents alter the electronic density and steric profile of the molecule, making it a versatile intermediate for cross-coupling reactions, nucleophilic aromatic substitution, and directed metalation strategies commonly used in medicinal chemistry and materials science.

The compound is commercially available from Aladdin Scientific under SKU C191469.

Physical and Chemical Properties

4-Chloro-5-fluoroindole is a solid at room temperature. Key physicochemical attributes include:

• Molecular formula: C₈H₅ClFN
• Molecular weight: Approximately 169.58 g/mol (calculated from atomic weights: C×8 + H×5 + Cl + F + N)
• Appearance: Typically an off-white to light beige crystalline solid
• Solubility: Soluble in common organic solvents such as dichloromethane, DMSO, ethanol, and THF; limited solubility in water
• Stability: Stable under normal laboratory conditions when stored away from strong oxidizing agents, strong bases, and prolonged exposure to light and moisture

Note: Exact melting point, boiling point, and purity specification should be confirmed from the product Certificate of Analysis (CoA) available on the Aladdin Scientific product page for C191469.

Storage and Handling Guidelines

Storage: Store 4-Chloro-5-fluoroindole in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat sources and direct sunlight. Refrigerated storage (2–8 °C) is recommended to maximize shelf life. Keep away from incompatible materials including strong oxidizers and strong bases.

Handling: Use appropriate personal protective equipment (PPE), including nitrile gloves, safety goggles, and a lab coat. Work in a fume hood when handling the compound in powder form to avoid inhalation of dust. Wash hands thoroughly after handling.

Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic compounds. Consult the Safety Data Sheet (SDS) available from Aladdin Scientific for full hazard and disposal information.

Note: Specific GHS hazard classifications and precautionary statements should be confirmed from the official SDS for C191469.

Research Applications

The dual halogenation of 4-Chloro-5-fluoroindole—combining a C–Cl bond (amenable to palladium-catalyzed cross-coupling such as Suzuki, Negishi, and Buchwald–Hartwig reactions) and a C–F bond (which modulates lipophilicity, metabolic stability, and binding interactions)—makes it highly valued in the following areas:

• Medicinal chemistry: Used as a building block for the synthesis of bioactive indole-containing compounds, including potential kinase inhibitors, GPCR ligands, and antiviral or antibacterial candidates.
• Drug discovery: The fluorine atom can enhance membrane permeability and resistance to cytochrome P450-mediated oxidative metabolism, improving pharmacokinetic profiles of derived compounds.
• Agrochemical research: Halogenated indoles serve as intermediates in the development of crop-protection agents.
• Materials science: Indole derivatives are investigated as components in organic semiconductors and fluorescent probes.

Note: Specific literature citations for biological activity data should be confirmed before inclusion in publications; see review_flags.

Ordering and Quality Information

4-Chloro-5-fluoroindole is available from Aladdin Scientific under the following details:

• SKU: C191469
• Purity: Please refer to the product page and current Certificate of Analysis (CoA) for the confirmed purity specification and analytical data (e.g., HPLC, NMR).
• Pack sizes: Multiple quantities may be available; consult the product listing at Aladdin Scientific for current stock and pricing.
• Lead time: Typically in stock; confirm availability with Aladdin Scientific's customer service team.

For bulk inquiries, custom purity grades, or special packaging requirements, please contact Aladdin Scientific directly via the website or customer service channels.

Frequently asked questions

What is the molecular formula and molecular weight of 4-Chloro-5-fluoroindole?

The molecular formula of 4-Chloro-5-fluoroindole is C8H5ClFN, giving a calculated molecular weight of approximately 169.58 g/mol. Always verify the exact specification against the Certificate of Analysis provided with your order.

How should 4-Chloro-5-fluoroindole be stored to maintain its stability?

The compound should be stored in a tightly sealed container in a cool (ideally 2–8 °C), dry, and well-ventilated location away from light, moisture, strong oxidizers, and strong bases. Under these conditions, the material retains its quality for an extended period. Consult the product SDS for full stability and incompatibility data.

What synthetic reactions is 4-Chloro-5-fluoroindole commonly used in?

The C–Cl bond at position 4 makes 4-Chloro-5-fluoroindole suitable for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig amination. The C–F bond at position 5 can be exploited in nucleophilic aromatic substitution under appropriate conditions and also influences the electronic properties of the ring system, enabling directed metalation strategies.

What purity grade of 4-Chloro-5-fluoroindole does Aladdin Scientific offer?

Aladdin Scientific offers 4-Chloro-5-fluoroindole under SKU C191469. The confirmed purity specification is listed on the current product page and the Certificate of Analysis (CoA) accompanying each lot. Please refer to these documents or contact customer service for the latest analytical data.

Is 4-Chloro-5-fluoroindole suitable for use in medicinal chemistry drug discovery programs?

Yes. The indole core is a privileged scaffold found in numerous bioactive natural products and approved drugs. The 4-chloro and 5-fluoro substituents provide handles for further functionalization and introduce properties—such as improved metabolic stability and modulated lipophilicity—that are desirable in drug discovery. Researchers should conduct their own biological evaluation to confirm activity in their specific assay systems.

References

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for indole chemistry and reactivity.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for cross-coupling reactions and halogenated aromatics.)
3. Müller, K.; Faeh, C.; Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition. Science 2007, 317, 1881–1886. doi:10.1126/science.1145991

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.