1,3-Cyclopentadiene

Agrochemicals 2025-03-02

1,3-Cyclopentadiene

Chemical Name: 1,3-Cyclopentadiene
Synonyms: Cyclopentadiene; Pentole
CAS Number: 542-92-7
Molecular Formula: C₅H₆
Molecular Weight: 66.10 g/mol

Physical and Chemical Properties

  • Appearance: Colorless to pale yellow liquid
  • Odor: Strong, sweet, turpentine-like
  • Melting Point: -85 °C (-121 °F)
  • Boiling Point: 41-42 °C (106-108 °F)
  • Density: 0.80 g/cm³ (at 25 °C)
  • Refractive Index: 1.444 (at 20 °C)
  • Vapor Pressure: 400 mmHg (at 20 °C)
  • Flash Point: -25 °C (-13 °F) (Highly flammable)
  • Solubility:
    • Insoluble in water
    • Miscible with organic solvents (ethanol, ether, acetone)

Chemical Properties

  • Reactivity:
    • Readily dimerizes at RT to form dicyclopentadiene (DCPD)
    • Acts as a diene in Diels-Alder reactions
    • Reacts violently with oxidizers
  • Stability:
    • Requires stabilizer (e.g., hydroquinone) for storage
    • Polymerizes exothermically above 30°C

Hazard and Safety Information (GHS)

  • Hazard Symbols:
    • F+ (Extremely flammable)
    • Xi (Irritant)
  • Hazard Statements:
    • H225: Highly flammable liquid and vapor
    • H304: May be fatal if swallowed and enters airways
    • H315: Causes skin irritation
    • H319: Causes serious eye irritation
    • H335: May cause respiratory irritation
  • Precautionary Measures:
    • P210: Keep away from heat/sparks/open flames
    • P301+P310: IF SWALLOWED: Immediately call poison center
    • P331: Do NOT induce vomiting
    • P403+P235: Store in well-ventilated place, keep cool

Storage & Handling

  • Store at ≤20°C under inert atmosphere (N₂/Ar)
  • Use explosion-proof refrigeration for bulk quantities
  • Stabilize with 100-200 ppm hydroquinone
  • Handle in fume hood with flame-proof equipment

Applications

  • Key monomer for synthetic rubbers
  • Precursor to cyclopentadienyl metal complexes (e.g., ferrocene)
  • Essential diene for Diels-Alder reactions

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