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2-Chloro-6-fluorobenzaldehyde (CAS No. 387-45-1): A Comprehensive Overview

1. Chemical and Physical Properties

• IUPAC Name: 2-Chloro-6-fluorobenzaldehyde
• Molecular Formula: C₇H₄ClFO
• Molecular Weight: 158.56 g/mol
• Physical State: White to yellow crystalline solid or liquid (depending on purity and conditions).
• Melting Point: 32–39 °C (lit.)
• Boiling Point: 92 °C (10 mmHg) or 203.8 °C (760 mmHg).
• Flash Point: 101 °C (closed cup).
• Density: 1.352 g/cm³.
• Solubility: Insoluble in water; soluble in organic solvents like DMF, dichloromethane, and ethyl acetate.
• Stability: Air-sensitive; prone to oxidation upon prolonged exposure.

2. Synthetic Routes

• From 2-Chloro-6-fluorotoluene:
  • Bromination/Oxidation: Heating with bromine followed by concentrated sulfuric acid.
  • Chromyl Chloride Oxidation: Reaction with CrO₂Cl₂ in carbon disulfide.
• Alternative Method: Catalytic chlorination of 2-chloro-6-fluorotoluene under metal halide lamp irradiation.

3. Applications

• Pharmaceuticals:
  • Key intermediate in the synthesis of flucloxacillin sodium (an antibiotic) and other β-lactam antibiotics.
  • Used in the preparation of chlorinated benzothiazepine derivatives via reactions such as thionation, aldimine condensation, and oxidative dearomatization.
• Agrochemicals:
  • Precursor for plant growth regulators like fluometuron and other herbicides.
• Organic Synthesis:
  • Building block for fluorinated/chlorinated aromatic compounds used in specialty chemicals and materials science.

4. Safety and Handling

• Hazard Classification:
  • GHS Labels: Skin irritation (Category 2), eye irritation (Category 2A), specific target organ toxicity (single exposure, Category 3), acute aquatic toxicity (Category 2).
  • Safety Precautions:
    • Wear appropriate PPE (gloves, goggles, face shield).
    • Avoid inhalation of dust/vapors; use in a fume hood.
    • Store in airtight containers, refrigerated, and away from moisture.
• Emergency Response:
  • Eye Contact: Rinse with water for ≥15 minutes.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.

5. Market Availability

• Suppliers: Manufacturers like Dayang Chem (Hangzhou) Co., Ltd., and Weifang Xingbei International Trade Co., Ltd., offer 95–99% purity grades at competitive prices (e.g., USD 1–2/kg).
• Packaging: Typically shipped in 25 g to 200 kg containers (e.g., iron-plastic drums).

6. Regulatory and Environmental Considerations

• Ecological Impact: Potential harm to aquatic life; avoid release into water bodies.
• Transportation: Classified as a hazardous material (irritant); adhere to IATA/IMDG regulations.

7. Analytical Data

• NMR/IR Spectroscopy: Characteristic peaks confirm molecular structure.
• Mass Spectrometry: Molecular ion peak at m/z 158 (M⁺).