Cyclopropane

Cyclopropane is classified as a saturated alicyclic hydrocarbon, yet its chemical reactivity is far greater than that of ordinary alkanes. Under standard temperature and pressure, it exists as a colorless, flammable gas with a faint ethereal sweetness. It is slightly soluble in water but readily miscible with organic solvents such as ethanol and diethyl ether. The most distinctive feature of cyclopropane is its significant angle strain resulting from its three-membered ring structure. Serving as a crucial three-carbon cyclic building block, cyclopropane is widely employed in the synthesis of pharmaceutical intermediates, agrochemicals, fragrances, and other fine chemicals.

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Product Introduction

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Physicochemical properties

Physical state: Gaseous (25℃), melting point −127.6℃, boiling point −32.9℃
Density: Gas 1.88 g/L (air ≈ 1.29), Liquid 0.720 g/cm³ (−33℃)
Solubility: Cyclopropane is sparingly soluble in water (approximately 0.2 g/100 mL at 20°C) and readily soluble in ethanol, diethyl ether, and petroleum ether;
Ring strain: The C–C–C bond angle is forced to compress to 60° (ideal sp³ 109.5°), Baeyer strain ~115 kJ/mol, giving cyclopropane both an alkane skeleton and some alkene reactivity
Bond characteristics: The C–C bond has a significant "banana bond" component, with an outward bulging electron cloud, making it easily attacked by electrophilic reagents; often treated as a "locked alkene" in the Hammond hypothesis
Flammability: Extremely flammable, explosion limits 2.4%–10.4% (air); burns with a blue flame to produce CO₂ + H₂O

Core Uses

Medical inhalation anesthesia (historical): Cyclopropane was used as a surgical anesthetic in the 1930s–1950s (MAC≈0.34 vol%), with rapid induction and good muscle relaxation; however, due to its extremely high explosion risk, it has been completely replaced by halothane, isoflurane, and sevoflurane, and is virtually extinct in modern clinical practice.
Organic synthesis building blocks: Replacing cyclopropane is a key ring system in pesticides (cycloproconazole, pyrethroid analogs), fragrances (ambromine precursors), and drugs (some antidepressant and antiviral side chains); parent cyclopropane is mostly used as a mechanistic research model.
High-energy fuel additives: High small ring strain and theoretical specific impulse; it was evaluated for use in rocket propellants, but its widespread adoption was limited due to storage stability and cost.

Safety and Storage

GHS: Extremely flammable gas (F+), high-pressure liquefied petroleum gas (storage and transportation in cylinders), asphyxiating. Explosion hazard: Wider flammability and explosion range than ethylene; explodes upon contact with a spark when mixed with air; strictly prohibited near open flames, static electricity, and high-temperature surfaces. Toxicity: Low toxicity, but high concentrations can cause anesthetic and respiratory depression; IDLH has no clearly defined value, managed as an asphyxiating gas. Storage: Pressure-resistant cylinders, cool and ventilated (<30℃), separate from oxidizers, halogens, and strong acids; dilute leaks with an explosion-proof fan, do not discharge into low-lying areas (heavier than air). Firefighting: After shutting off the gas supply, use dry powder or CO₂; if water is scarce, shut off the gas supply first.

FAQ

Q: Toxicity and Occupational Health

A:Low acute toxicity: Inhalation LCLo in mice is 282 g/m³ over 2 hours; classified as a gas of low toxicity.

Primary hazards are not toxicity, but rather asphyxiation and explosion:

High concentrations displace air, causing simple asphyxiation;

Contact with the liquid causes frostbite (due to heat absorption during rapid vaporization);

Vapors have weak irritant effects; not classified as carcinogenic or teratogenic.

No specific occupational exposure limit exists; strictly controlled by analogy to "flammable gases."

Q: Key Points for Handling and Storage

A: Explosion-proof ventilation + static grounding + no open flames; use explosion-proof electrical equipment and tools;

PPE: Cold-resistant gloves (for liquid contact), safety goggles, half-mask respirator (use SCBA for high concentrations);

Storage: Cool, ventilated warehouse dedicated to flammable gases (≤30°C); store cylinders upright and secured; keep strictly isolated from oxidizers and halogens;

Leakage: Cut off the gas source; use water spray for dilution (note its low solubility); evacuate personnel upwind;

Firefighting: Cut off the gas source, then extinguish using dry powder or CO₂; if the source cannot be cut off, allow the flame to burn out naturally while preventing flashback.

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