3-Amino-5-fluoropyridine: Properties, Uses & FAQs

3-Amino-5-fluoropyridine is a fluorine-substituted aminopyridine building block widely employed in medicinal chemistry and pharmaceutical synthesis as a versatile heterocyclic intermediate.

CAS Number

71902-33-5

Molecular Formula

C₅H₅FN₂

Molecular Weight

112.10 g/mol

Appearance

White to off-white crystalline solid

Recommended Storage

Store in a cool, dry place away from light and moisture; seal tightly after use

Aladdin SKU

A119622

What Is 3-Amino-5-fluoropyridine?

3-Amino-5-fluoropyridine (CAS 71902-33-5) is a difunctionalised pyridine derivative bearing a primary amino group at the 3-position and a fluorine atom at the 5-position of the pyridine ring. Its molecular formula is C₅H₅FN₂ with a molecular weight of 112.10 g/mol. The simultaneous presence of the electron-withdrawing fluorine substituent and the nucleophilic amino group makes this compound a highly reactive and versatile scaffold for constructing more complex heterocyclic architectures. It is commonly encountered as a white to off-white crystalline powder and is soluble in polar organic solvents such as dimethyl sulfoxide (DMSO), ethanol, and methanol.

Key Research and Synthetic Applications

3-Amino-5-fluoropyridine serves as an important building block and pharmaceutical intermediate in several areas of synthetic and medicinal chemistry:

• Pharmaceutical synthesis: The amino group can participate in amide coupling, reductive amination, and cyclisation reactions, enabling access to a broad range of drug candidates and bioactive molecules.
• Cross-coupling chemistry: The pyridine ring and the C–F bond can be exploited in palladium-catalysed coupling reactions, nucleophilic aromatic substitution (SNAr), and other transition-metal-mediated transformations.
• Agrochemical research: Fluorinated pyridine scaffolds are frequently incorporated into crop-protection compounds to modulate biological activity and metabolic stability.
• Material science: Aminofluoropyridines are used as ligands and precursors in the preparation of coordination polymers and functional materials.

The fluorine atom at the 5-position exerts a strong inductive effect on the ring, influencing both the reactivity of the amino group and the overall electron density of the heterocycle, which researchers exploit to fine-tune pharmacokinetic and physicochemical properties.

Handling, Safety, and Storage Guidelines

Although 3-Amino-5-fluoropyridine is a solid reagent, appropriate laboratory precautions should always be observed:

• Personal protective equipment: Wear nitrile gloves, safety goggles, and a lab coat when handling. A dust mask or fume hood is recommended when weighing powder quantities.
• Storage: Store in a tightly sealed container in a cool (typically 2–25 °C), dry location away from direct light, moisture, and incompatible reagents such as strong acids, strong oxidisers, and reactive acyl halides.
• Stability: The compound is generally stable under recommended storage conditions. Prolonged exposure to air and humidity may cause discolouration; re-seal containers promptly after use.
• Disposal: Dispose of waste in accordance with local regulations for organic nitrogen- and fluorine-containing compounds.

Always consult the Safety Data Sheet (SDS) supplied with the product for full hazard information before use.

Purity, Specification, and Quality Assurance

Aladdin Scientific offers 3-Amino-5-fluoropyridine (SKU: A119622) as a research-grade reagent. Quality control typically includes:

• Purity assessment by high-performance liquid chromatography (HPLC) or gas chromatography (GC) to confirm identity and purity grade.
• Structural confirmation by nuclear magnetic resonance (NMR) spectroscopy and/or mass spectrometry.
• Certificate of Analysis (CoA): A lot-specific CoA is available upon request and provides the actual measured purity, appearance, and other critical specifications for each batch.

Researchers requiring specific purity grades or custom quantities are encouraged to contact Aladdin Scientific's technical support team for further assistance.

Ordering and Availability

3-Amino-5-fluoropyridine is available from Aladdin Scientific under SKU A119622. Orders can be placed directly through the Aladdin Scientific website or by contacting our sales team. Key ordering information:

• Pack sizes: Multiple pack sizes are typically available to suit both small-scale exploratory research and larger preparative needs — please check the product page for current stock and pricing.
• Lead time: In-stock items generally ship within 1–3 business days; please verify real-time availability on the product listing.
• Export and regulatory compliance: Customers outside mainland China should confirm any applicable import regulations for nitrogen-containing heterocyclic compounds in their jurisdiction prior to ordering.

Frequently asked questions

What is the CAS number for 3-Amino-5-fluoropyridine?

The CAS registry number for 3-Amino-5-fluoropyridine is 71902-33-5. This number can be used to unambiguously identify the compound when searching chemical databases or placing orders.

What solvents are suitable for dissolving 3-Amino-5-fluoropyridine?

3-Amino-5-fluoropyridine is generally soluble in polar organic solvents including DMSO, ethanol, and methanol. Solubility in water is limited. For stock solutions, DMSO is frequently chosen for biological assays due to its high solvating power and compatibility with most cell-based systems at low concentrations.

How should 3-Amino-5-fluoropyridine be stored to maintain stability?

Store 3-Amino-5-fluoropyridine in a tightly sealed container in a cool, dry place away from light and moisture. Recommended storage temperatures are typically between 2 °C and 25 °C. Avoid exposure to strong acids, oxidising agents, and humid conditions, which can accelerate degradation or discolouration.

What are the main synthetic uses of 3-Amino-5-fluoropyridine in medicinal chemistry?

In medicinal chemistry, 3-Amino-5-fluoropyridine is valued as a bifunctional building block. The primary amino group enables amide couplings, sulfonamide formation, and ring-closure reactions to form bicyclic heterocycles, while the C–F bond at the 5-position can undergo nucleophilic aromatic substitution (SNAr) or serve as a handle for further functionalisation. The fluorine atom also improves the metabolic stability and lipophilicity of resulting drug candidates.

Is a Certificate of Analysis (CoA) available for Aladdin's 3-Amino-5-fluoropyridine (A119622)?

Yes. A lot-specific Certificate of Analysis is available for A119622 upon request. The CoA details the measured purity, appearance, and other critical quality parameters for the specific batch supplied. Contact Aladdin Scientific's customer service or visit the product page to download or request your CoA.

Can 3-Amino-5-fluoropyridine be used in palladium-catalysed cross-coupling reactions?

Yes, the pyridine scaffold of 3-Amino-5-fluoropyridine is compatible with several palladium-catalysed transformations. The C–F bond can participate in certain transition-metal-mediated C–F activation reactions, and the amino group can be converted to a diazonium salt or used directly in coupling protocols. Researchers should optimise reaction conditions (catalyst loading, ligand, base, and solvent) based on the specific coupling target.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for nucleophilic aromatic substitution and heterocyclic chemistry.)
2. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: Chichester, 2009. (Reference for the role of fluorine substituents in drug design and metabolic stability.)
3. Aladdin Scientific Product Page: 3-Amino-5-fluoropyridine, SKU A119622. https://www.aladdin-e.com (accessed 2024).

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