Ethynylcyclopropane

C5H6

ethynylcyclopropane

CAS6746-94-7
GHS02 Gefahrensymbol: Entzündbar – Flamme
GHS05 Gefahrensymbol: Ätzend – Ätzwirkung
Danger

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Identification

CAS Number
6746-94-7
EC Number
425-430-1
UN Number
3295
Index Number
601-076-00-3
PubChem CID
138823

Physical-chemical properties

Molecular Formula
C5H6
Molar Mass
66.10 g/mol
IUPAC Name
ethynylcyclopropane

Chemical Identifiers

InChI
InChI=1S/C5H6/c1-2-5-3-4-5/h1,5H,3-4H2
InChI Key
NPTDXPDGUHAFKC-UHFFFAOYSA-N

Overview

Ethynylcyclopropane (CAS 6746-94-7) is a highly reactive cyclic alkyne compound with significant synthetic utility in organic chemistry applications. This specialized chemical compound represents a unique structural combination featuring both a three-membered cyclopropyl ring and a terminal alkyne functional group within its C5H6 molecular framework. With a molecular weight of 66.1 g/mol, ethynylcyclopropane exhibits remarkable reactivity due to the inherent ring strain of the cyclopropane moiety combined with the electrophilic nature of the alkyne functionality. This dual reactivity makes it particularly valuable for advanced synthetic transformations and cycloaddition reactions. The compound requires careful handling protocols due to its classification as a flammable liquid (Category 2) and its potential for causing serious eye damage and skin irritation. Storage must comply with ADR Class 3 requirements for flammable liquids, with appropriate fire prevention measures and personal protective equipment mandatory during handling operations. The GHS02 and GHS05 pictograms clearly indicate both fire and corrosion hazards that technical personnel must address through proper safety procedures. In industrial applications, ethynylcyclopropane serves primarily as a specialized building block for pharmaceutical intermediates and fine chemical synthesis. Its unique reactivity profile makes it valuable for preparing complex cyclic compounds through ring-opening reactions and cycloaddition processes. The compound also finds utility in materials science research, particularly in developing novel polymeric materials where its dual functionality enables controlled crosslinking reactions. Unlike simpler compounds such as prop-2-enenitrile, ethynylcyclopropane offers enhanced synthetic versatility through its cyclopropyl-alkyne combination. OYSI maintains reliable supply chains for ethynylcyclopropane to support European research institutions and specialty chemical manufacturers requiring this advanced synthetic intermediate.

Safety & Classification

Danger
Classification:

Flam. Liq. 2; Skin Irrit. 2; Eye Dam. 1; Aquatic Chronic 3

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H225

Highly flammable liquid and vapour.

H315

Causes skin irritation.

H318

Causes serious eye damage.

H412

Harmful to aquatic life with long lasting effects.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Skin Contact

Irritant

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Eye Contact

Harmful

Measures if substance gets into the eyes

First Aid Actions

  • +P305IF IN EYES:
  • +P351Rinse cautiously with water for several minutes.
  • +P338Remove contact lenses, if present and easy to do. Continue rinsing.
  • +P313Get medical advice/attention.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number3295
ADR Class3
Packing GroupII
Tunnel CodeD/E
Proper Shipping NameEthinylcyclopropan
Marine PollutantNo

Frequently Asked Questions

What is ethynylcyclopropane?

Ethynylcyclopropane is an organic compound with the molecular formula C5H6 and CAS number 6746-94-7. This cyclic hydrocarbon features a three-membered cyclopropane ring with an attached ethynyl group (acetylene functionality). With a molecular weight of 66.1 g/mol, it represents a highly strained and reactive molecule due to the combination of cyclopropane ring tension and the triple bond functionality, making it valuable in specialized organic synthesis applications.

What are the physicochemical properties of ethynylcyclopropane?

Ethynylcyclopropane is a volatile organic liquid at room temperature with high flammability characteristics. The compound exhibits typical properties of strained cyclic acetylenes, including reactivity toward addition reactions. Its low molecular weight (66.1 g/mol) and hydrocarbon structure suggest limited water solubility but good solubility in organic solvents. The presence of both cyclopropane strain and acetylene functionality makes it thermodynamically unstable and prone to polymerization or rearrangement reactions.

What is ethynylcyclopropane used for?

Ethynylcyclopropane is primarily used as a specialized building block in organic synthesis and pharmaceutical research. Its unique structural features make it valuable for preparing complex cyclic compounds through ring-opening reactions and cycloaddition processes. The compound serves as an intermediate in the synthesis of bioactive molecules and specialty chemicals. Its reactivity profile makes it particularly useful in academic research for studying strained ring systems and developing new synthetic methodologies.

How to handle ethynylcyclopropane safely?

Ethynylcyclopropane requires careful handling due to its flammable nature and potential for skin and eye irritation. Personal protective equipment must include chemical-resistant gloves, safety goggles, and appropriate clothing to prevent skin contact. Work should be conducted in well-ventilated areas or under fume hoods, away from ignition sources. The compound can cause severe eye damage and skin irritation, requiring immediate attention if contact occurs. Ground all equipment to prevent static electricity buildup.

How to store ethynylcyclopropane correctly?

Ethynylcyclopropane must be stored in a cool, dry, well-ventilated area away from heat sources, sparks, and open flames. Keep containers tightly sealed and use appropriate secondary containment. Store separately from oxidizing agents, acids, and bases due to potential incompatibilities. Temperature control is essential to prevent decomposition or polymerization. Use explosion-proof electrical equipment in storage areas and maintain proper grounding. Regular inspection of containers for leaks or deterioration is recommended.

What to do in case of contact with ethynylcyclopropane?

Ethynylcyclopropane contact requires immediate action due to its irritating properties. For skin contact, immediately remove contaminated clothing and flush the affected area with plenty of water for at least 15 minutes. In case of eye contact, rinse immediately with water for at least 15 minutes and seek immediate medical attention as the compound can cause severe eye damage. If inhaled, move the person to fresh air immediately. Seek medical attention for all exposure incidents.

How to dispose of ethynylcyclopropane properly?

Ethynylcyclopropane disposal must comply with local, national, and EU waste regulations as a hazardous chemical waste. The compound cannot be disposed of in regular waste streams due to its flammability and environmental impact. Contact licensed hazardous waste disposal companies for proper treatment, which typically involves incineration at high temperatures in specialized facilities. Small quantities may require neutralization or reaction to less hazardous compounds before disposal. Always consult current waste disposal regulations and safety data sheets.

How to transport ethynylcyclopropane?

Ethynylcyclopropane is classified as ADR Class 3 (flammable liquids), Packing Group II, indicating moderate danger level for transport. Transportation requires appropriate UN-specification packaging designed for flammable liquids. Vehicles must carry proper placarding and documentation, and drivers need ADR certification. The compound requires segregation from incompatible materials during transport. Emergency response information must accompany shipments, and transport should avoid extreme temperatures to prevent vapor pressure buildup or decomposition.

Is ethynylcyclopropane subject to specific regulations?

Ethynylcyclopropane is subject to standard EU chemical regulations including REACH registration requirements and CLP classification. The compound is classified under GHS with specific hazard categories (Flam. Liq. 2, Skin Irrit. 2, Eye Dam. 1, Aquatic Chronic 3) requiring appropriate labeling and safety data sheets. It is not currently listed as a Substance of Very High Concern (SVHC). Users must comply with occupational exposure limits and industrial emissions regulations where applicable.

Where to buy ethynylcyclopropane in Europe?

Ethynylcyclopropane is available through OYSI, a specialized European distributor of technical chemicals serving research institutions and industrial customers. As a niche specialty chemical, it requires sourcing from suppliers experienced in handling reactive compounds. OYSI provides proper documentation, safety data sheets, and regulatory compliance support for European customers. Due to its specialized nature and handling requirements, availability may be subject to minimum order quantities and lead times for custom synthesis or importation.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.