Aziridine

C2H5N

aziridine

CAS151-56-4
GHS02 Gefahrensymbol: Entzündbar – Flamme
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS05 Gefahrensymbol: Ätzend – Ätzwirkung
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
Danger

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Identification

CAS Number
151-56-4
EC Number
205-793-9
UN Number
1185
Index Number
613-001-00-1
PubChem CID
9033

Physical-chemical properties

Molecular Formula
C2H5N
Molar Mass
43.07 g/mol
IUPAC Name
aziridine

Chemical Identifiers

InChI
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
InChI Key
NOWKCMXCCJGMRR-UHFFFAOYSA-N

Overview

Aziridine (CAS 151-56-4) is a three-membered heterocyclic amine compound with highly reactive ring-strain properties and significant industrial importance. This highly strained nitrogen-containing heterocycle represents one of the smallest cyclic amines in organic chemistry, featuring exceptional reactivity due to its angular strain and the nucleophilic nature of the nitrogen atom. The molecule's three-membered ring structure creates substantial ring tension, making it considerably more reactive than larger cyclic amines and leading to its utility as a versatile chemical intermediate in various synthetic applications. Aziridine exhibits remarkable chemical versatility, readily undergoing ring-opening reactions with nucleophiles, electrophiles, and various catalysts. This reactivity profile makes it valuable for polymer synthesis, pharmaceutical intermediates, and specialty chemical manufacturing. The compound's ability to polymerize and cross-link other materials has established its role in advanced materials science and surface modification applications. Safety considerations are paramount when handling aziridine, as it presents multiple hazards including high acute toxicity, carcinogenic potential, and mutagenic properties. The substance requires specialized handling procedures, appropriate personal protective equipment, and controlled storage conditions. Its classification under ADR Class 6.1 reflects its significant toxicity profile, while its flammable nature demands additional fire safety precautions. Industrial applications primarily focus on its use as a chemical intermediate in pharmaceutical synthesis, polymer cross-linking agent production, and specialty coating formulations. Like related reactive compounds such as 2-(chloromethyl)oxirane, aziridine serves as a key building block for creating more complex molecular structures in fine chemical synthesis. OYSI provides aziridine to qualified industrial customers with comprehensive safety documentation and technical support for specialized chemical applications.

Safety & Classification

Danger
Classification:

Flam. Liq. 2; Carc. 1B; Muta. 1B; Acute Tox. 2 *; Acute Tox. 1; Acute Tox. 2 *; Skin Corr. 1B; Aq...

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H225

Highly flammable liquid and vapour.

H350

May cause cancer.

H340

May cause genetic defects.

H330

Fatal if inhaled.

H310

Fatal in contact with skin.

H300

Fatal if swallowed.

H314

Causes severe skin burns and eye damage.

H411

Toxic 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

Inhalation

Fatal

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Fatal

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:

Ingestion

Fatal

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

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 Number1185
ADR Class6.1
Packing GroupI
Tunnel CodeC/D
Proper Shipping NameEthylenimin, stabilisiert
Marine PollutantNo

Frequently Asked Questions

What is aziridine?

Aziridine is a highly reactive heterocyclic organic compound with the molecular formula C2H5N and a molecular weight of 43.07 g/mol. It consists of a three-membered ring containing one nitrogen atom and two carbon atoms. This strained ring structure makes aziridine extremely reactive and chemically unstable. The compound is classified as highly hazardous due to its carcinogenic, mutagenic, and acutely toxic properties, requiring strict safety protocols for handling and use.

What are the physicochemical properties of aziridine?

Aziridine is a colorless liquid at room temperature with a characteristic ammonia-like odor. It has a low boiling point and is highly volatile, contributing to its flammable nature (classified as Flam. Liq. 2). The compound is highly water-soluble and miscible with most organic solvents. Its three-membered ring structure creates significant ring strain, making it extremely reactive toward nucleophiles. Aziridine readily polymerizes and can undergo ring-opening reactions under mild conditions.

What is aziridine used for?

Aziridine is primarily used as a chemical intermediate in the production of specialty polymers, particularly polyethylenimine and cross-linking agents. It serves as a building block for pharmaceuticals, agrochemicals, and textile finishing agents. The compound is utilized in the synthesis of anticancer drugs and as a sterilizing agent for medical equipment. Due to its high reactivity, aziridine is also employed in polymer modification and as a cross-linking agent for coatings and adhesives.

How to handle aziridine safely?

Aziridine requires extreme caution during handling due to its multiple hazard classifications including acute toxicity, carcinogenicity, and corrosivity. Personnel must wear full personal protective equipment including chemical-resistant gloves, protective clothing, and respiratory protection. Work should be conducted in a well-ventilated area or under a fume hood. Avoid contact with skin, eyes, and inhalation of vapors. Use non-sparking tools due to its flammable nature and ensure proper grounding to prevent static discharge.

How to store aziridine correctly?

Aziridine must be stored in a cool, dry, well-ventilated area away from heat sources, sparks, and open flames due to its flammable properties. Use only approved containers resistant to corrosion, as aziridine is classified as Skin Corr. 1B. Store separately from oxidizing agents, acids, and bases to prevent dangerous reactions. Temperature control is critical to prevent polymerization and pressure buildup. Access should be restricted to authorized personnel only due to its carcinogenic and mutagenic properties.

What to do in case of contact with aziridine?

Aziridine contact requires immediate emergency response due to its acute toxicity and corrosive nature. For skin contact, immediately remove contaminated clothing and flush affected area with copious amounts of water for at least 15 minutes. In case of eye contact, rinse thoroughly with water and seek immediate medical attention. If inhaled, move person to fresh air immediately and provide artificial respiration if necessary. For ingestion, do not induce vomiting and seek immediate medical attention while providing supportive care.

How to dispose of aziridine properly?

Aziridine disposal must comply with strict hazardous waste regulations due to its carcinogenic and toxic properties. The compound cannot be disposed of through normal waste streams and requires specialized hazardous waste treatment facilities. Contact licensed waste disposal companies experienced in handling carcinogenic substances. Small quantities may be neutralized through controlled chemical treatment under proper safety conditions. All disposal activities must be documented and reported according to local environmental regulations and REACH requirements.

How to transport aziridine?

Aziridine is classified under ADR Class 6.1 (toxic substances) Packing Group I, indicating its high toxicity level. Transportation requires specialized hazardous materials packaging, proper labeling with GHS pictogrammes (GHS02, GHS08, GHS06, GHS05, GHS09), and appropriate shipping documentation. Only certified carriers experienced in handling toxic and flammable substances should transport aziridine. Vehicles must be equipped with appropriate emergency equipment and drivers must have hazardous materials certification. Temperature control during transport is essential to prevent polymerization.

Is aziridine subject to specific regulations?

Aziridine is subject to extensive regulatory oversight due to its carcinogenic (Carc. 1B) and mutagenic (Muta. 1B) properties under CLP regulation. It requires registration under REACH with detailed safety assessments and exposure scenarios. The compound may be subject to authorization procedures and use restrictions in certain applications. Workers handling aziridine must receive specialized training and health monitoring. Industrial users must implement strict occupational exposure limits and report usage to regulatory authorities in many jurisdictions.

Where to buy aziridine in Europe?

Aziridine is available through specialized chemical distributors experienced in handling highly hazardous substances. OYSI, as a European chemical distributor, can provide aziridine to qualified industrial customers with proper safety protocols and regulatory compliance. Due to its hazardous nature, purchase requires verification of proper handling facilities, trained personnel, and legitimate industrial use. Buyers must demonstrate compliance with REACH requirements and local safety regulations before procurement of this controlled substance.

Data Sources

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