3-CYANO-5-FLUOROPYRIDINE NEW

5-Fluoro-3-cyanopyridine (CAS No.: 696-42-4) – Technical Analysis and Industrial Applications of Fluorinated Pyridine Intermediates

I. Basic Information and Physicochemical Properties

1. Key Chemical Parameters

• Chinese Name: 5-Fluoro-3-cyanopyridine

• English Name: 5-Fluoro-3-cyanopyridine

• CAS No.: 696-42-4

• Molecular Formula: $C_6{H}_{3}F{N}_2$

• Molecular Weight: 122.09

• Appearance: White to off-white crystalline powder, odorless, stable in air.

2. Physicochemical Properties

• Cyanide (-CN) group can hydrolyze to 5-fluoronicotinic acid (CAS: 393-52-2) or reduce to 5-fluoronicotinamide (CAS: 2927-71-1).

• Fluorine atom on the pyridine ring is susceptible to nucleophilic substitution (e.g., reactions with amines, alcohols) due to the electron-withdrawing effect of the cyanide group.

• Melting Point: 82-84℃

• Boiling Point: 265-267℃ (atmospheric pressure)

• Density: 1.32 g/cm³

• Solubility: Highly soluble in methanol, ethanol, acetonitrile; slightly soluble in water (≈0.3g/100mL at 25℃); insoluble in n-hexane.

• Chemical Reactivity:

• Stability: Stable at room temperature; avoid contact with strong acids/bases or oxidizers; no significant decomposition under light.

II. Upstream and Downstream Industry Chain Analysis

1. Upstream Raw Materials and Synthesis Process

• 3-Cyanopyridine reacts with DAST or anhydrous HF at 0-20℃, followed by column chromatography or recrystallization (ethanol/water system) to yield ≥99% purity product with 65-70% yield.

• Reaction Equation: $C_6{H}_4{N}_2+F^{+}\to C_6{H}_{3}F{N}_2+H^{+}$

• Core Raw Materials: 3-Cyanopyridine (CAS: 100-54-9), Fluorinating Agents (e.g., DAST, anhydrous HF).

• Mainstream Synthesis Route:
  Electrophilic Fluorination Method:

2. Downstream Products and Derivatives

• Ligand for metal-organic frameworks (MOFs); organic optoelectronic materials (e.g., OLED hole transport layers).

• Production of fluorinated pyridine herbicides (e.g., Fluridone intermediates), insecticides (e.g., Fipronil analogs), and insect feeding deterrents.

• Synthesis of antifungal drugs (e.g., Voriconazole intermediates), antiviral drugs (e.g., HIV integrase inhibitor precursors), and novel anticancer drugs (e.g., PI3K/mTOR dual inhibitors).

• Pharmaceutical Intermediates:

• Agrochemical Intermediates:

• Materials Science:

III. Key Application Areas

1. Pharmaceutical R&D and Innovative Drugs

• Serves as a pyridine scaffold for PI3K/mTOR dual inhibitors (e.g., Everolimus derivatives), suppressing tumor angiogenesis and proliferation.

• Reacted with nucleoside analogs to produce HIV integrase inhibitors (e.g., Dolutegravir intermediates), blocking viral DNA integration into host genomes.

• Hydrolyzed to 5-fluoronicotinic acid, condensed with 2,4-difluoroaniline to form Voriconazole intermediates, treating invasive aspergillosis with >85% clinical efficacy.

• Antifungal Drug Intermediate:

• Antiviral Drug Precursor:

• Anticancer Drug Synthesis:

2. Agrochemical Innovation and Green Pest Control

• Fluorine and cyanide substitutions enhance contact activity against aphids and thrips, inhibiting GABA receptors with 1/3 the dosage of traditional insecticides.

• Condensed with triazines to form Fluridone intermediates, inhibiting carotenoid synthesis in cotton and soybean fields, providing 8-12 weeks of weed control.

• High-Efficiency Herbicide Intermediate:

• Novel Insecticide Development:

3. Materials Science and Catalysis

• Copolymerized with carbazoles to form hole transport layers in perovskite solar cells, boosting power conversion efficiency (PCE) to 22% and stability >1000 hours.

• Nitrogen atoms coordinate with metal ions (e.g., Zn²⁺, Cu²⁺) to create selective gas adsorption materials for CO₂ capture (1.2mmol/g capacity at 25℃, 1bar).

• MOFs Ligand:

• Organic Optoelectronic Materials:

IV. Technical Advantages and Market Dynamics

• Technical Barriers:

• Electrophilic fluorination requires precise control of reagent dosage and temperature to avoid polyfluorinated byproducts. Microwave-assisted synthesis shortens reaction time to 2 hours, increasing yield to 75%.

• Production Capacity:

• Global capacity ≈50 tons/year, with China accounting for 60%. Major producers include Jiangsu Yangnong Chemical and Zhejiang Lianhua Technology, primarily using DAST fluorination. Green fluorination (e.g., electrochemical methods) is under exploration.

• Market Demand:

• Driven by antifungal drugs, novel agrochemicals, and MOFs materials, 2024 demand grew 19% YoY. The 2025 market is projected to exceed $25 million, with pharmaceuticals dominating 60%.

V. Safety and Storage Recommendations

• Hazards:

• Dust irritates eyes and respiratory tract; oral LD50 >2000mg/kg (low toxicity). Wear N95 respirators and nitrile gloves during handling.

• Storage Conditions:

• Store in sealed, cool, dry conditions (≤25℃) using moisture-proof packaging (aluminum foil bags or plastic-lined cardboard drums). Avoid oxidizers and acids; shelf life up to 2 years.

VI. SEO Optimization Strategy

1. Keyword Layout

• Core Keywords: 5-Fluoro-3-cyanopyridine, 696-42-4, fluorinated pyridine intermediate, Voriconazole raw material, Fluridone intermediate.

• Long-Tail Keywords: 5-Fluoro-3-cyanopyridine synthesis process, antifungal drug intermediate, MOFs ligand material.

• Chinese-English Combinations: 5-Fluoro-3-cyanopyridine, CAS 696-42-4, Pyridine intermediate.

Translation Notes:

1. Technical terms (e.g., CAS numbers, chemical names) are retained in English for standardization.

2. Units and symbols (e.g., ℃, g/cm³) follow international conventions.

3. Chemical equations and structures are preserved for scientific accuracy.