1,3-Cyclopentadiene

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 liquidOdor: Strong, sweet, turpentine-likeMelting 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 waterMiscible with organic solvents (ethanol, ether, acetone)

Chemical Properties

Reactivity:Readily dimerizes at RT to form dicyclopentadiene (DCPD)Acts as a diene in Diels-Alder reactionsReacts violently with oxidizersStability:Requires stabilizer (e.g., hydroquinone) for storagePolymerizes exothermically above 30°C

Hazard and Safety Information (GHS)

Hazard Symbols:F+ (Extremely flammable)Xi (Irritant)Hazard Statements:H225: Highly flammable liquid and vaporH304: May be fatal if swallowed and enters airwaysH315: Causes skin irritationH319: Causes serious eye irritationH335: May cause respiratory irritationPrecautionary Measures:P210: Keep away from heat/sparks/open flamesP301+P310: IF SWALLOWED: Immediately call poison centerP331: Do NOT induce vomitingP403+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 quantitiesStabilize with 100-200 ppm hydroquinoneHandle in fume hood with flame-proof equipment

Applications

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

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