2-(chloromethyl)oxirane

C3H5ClO

CAS106-89-8
GHS02 Gefahrensymbol: Entzündbar – Flamme
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS05 Gefahrensymbol: Ätzend – Ätzwirkung
Danger

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Identification

CAS Number
106-89-8
EC Number
203-439-8
UN Number
2023
Index Number
603-026-00-6
PubChem CID
7835

Physical-chemical properties

Molecular Formula
C3H5ClO
Molar Mass
92.52 g/mol
IUPAC Name
2-(chloromethyl)oxirane

Chemical Identifiers

InChI
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
InChI Key
BRLQWZUYTZBJKN-UHFFFAOYSA-N

Overview

2-(chloromethyl)oxirane (CAS 106-89-8) is a highly reactive chlorinated epoxide compound with significant industrial applications and severe health hazards. This three-membered cyclic ether, also known by its IUPAC designation, represents a critical intermediate in chemical manufacturing processes where its unique reactivity profile makes it valuable for specialized synthetic pathways. As a member of the epoxide family, 2-(chloromethyl)oxirane exhibits the characteristic ring strain of oxiranes, making it exceptionally reactive toward nucleophilic attack. The presence of the chloromethyl substituent further enhances its reactivity, distinguishing it from simpler epoxides and making it more versatile than related compounds such as aziridine in certain applications. With a molecular formula of C3H5ClO and molecular weight of 92.52 g/mol, this colorless liquid demonstrates the dual functionality that makes chlorinated epoxides particularly useful in industrial chemistry. The compound presents significant safety considerations, classified under multiple hazard categories including carcinogenicity (Category 1B), acute toxicity, skin corrosion, and flammability. Its GHS classification requires stringent handling protocols, specialized storage conditions, and comprehensive safety measures in industrial environments. The ADR Class 6.1 designation reflects its toxic nature during transport and storage. Primary industrial applications include its use as an intermediate in pharmaceutical synthesis, as a chemical building block for specialty polymers, and in the production of various fine chemicals where its bifunctional reactivity enables complex molecular construction. The compound's ability to participate in ring-opening reactions while maintaining the reactive chloromethyl group makes it particularly valuable in multi-step synthetic processes. OYSI provides reliable access to 2-(chloromethyl)oxirane for qualified industrial customers with appropriate handling capabilities and regulatory compliance.

Safety & Classification

Danger
Classification:

Flam. Liq. 3; Carc. 1B; Acute Tox. 3 *; Acute Tox. 3 *; Acute Tox. 3 *; Skin Corr. 1B; Skin Sens. 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H226

Flammable liquid and vapour.

H350

May cause cancer.

H331

Toxic if inhaled.

H311

Toxic in contact with skin.

H301

Toxic if swallowed.

H314

Causes severe skin burns and eye damage.

H317

May cause an allergic skin reaction.

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

Toxic

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

Toxic

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

Toxic

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 Number2023
ADR Class6.1
Packing GroupII
Tunnel CodeD/E
Proper Shipping NameEpichlorhydrin
Marine PollutantNo

Frequently Asked Questions

What is 2-(chloromethyl)oxirane?

2-(chloromethyl)oxirane is an organochlorine compound with the molecular formula C3H5ClO and CAS number 106-89-8. This chemical features both an epoxide ring and a chloromethyl group, making it a highly reactive intermediate. With a molecular weight of 92.52 g/mol, it is classified as a dangerous substance due to its carcinogenic properties, flammability, and corrosive nature. It requires careful handling under controlled conditions due to its multiple hazard classifications.

What are the physicochemical properties of 2-(chloromethyl)oxirane?

2-(chloromethyl)oxirane is a colorless liquid at room temperature with a characteristic pungent odor. The compound is moderately soluble in water and miscible with most organic solvents due to its polar chlorine atom and epoxide functionality. It has a relatively low boiling point and high vapor pressure, contributing to its flammable liquid classification. The presence of both electrophilic centers makes it highly reactive toward nucleophiles.

What is 2-(chloromethyl)oxirane used for?

2-(chloromethyl)oxirane serves as a crucial intermediate in organic synthesis and chemical manufacturing. It is primarily used in the production of epoxy resins, pharmaceuticals, and specialty chemicals. The compound acts as an alkylating agent in various synthetic pathways and is employed in the manufacture of glycerol derivatives. Its dual reactive sites make it valuable for creating cross-linked polymer networks and in the synthesis of complex organic molecules.

How to handle 2-(chloromethyl)oxirane safely?

2-(chloromethyl)oxirane requires strict safety protocols due to its corrosive and carcinogenic nature. Personnel must wear full chemical-resistant suits, nitrile gloves, and respiratory protection with appropriate filters. Work should be conducted in well-ventilated areas or under fume hoods to prevent vapor exposure. Eye protection and emergency shower facilities must be readily available. All handling procedures should minimize skin contact and inhalation risks through proper engineering controls.

How to store 2-(chloromethyl)oxirane correctly?

2-(chloromethyl)oxirane must be stored in tightly sealed containers in a cool, dry, well-ventilated area away from heat sources and ignition points. The storage area should be equipped with appropriate fire suppression systems and maintained below 25°C. Keep away from strong bases, acids, and nucleophilic compounds that could trigger unwanted reactions. Secondary containment is recommended, and storage areas should be restricted to authorized personnel only with appropriate hazard signage.

What to do in case of contact with 2-(chloromethyl)oxirane?

Immediate action is required for any contact with 2-(chloromethyl)oxirane due to its corrosive properties. For skin contact, immediately flush the affected area with copious amounts of water for at least 15 minutes and remove contaminated clothing. In case of eye contact, rinse continuously with water and seek immediate medical attention. If inhaled, move the person to fresh air immediately. For ingestion, do not induce vomiting and seek emergency medical care immediately.

How to dispose of 2-(chloromethyl)oxirane properly?

2-(chloromethyl)oxirane disposal must comply with hazardous waste regulations due to its carcinogenic classification. The compound should be collected in appropriate hazardous waste containers and disposed of through licensed hazardous waste treatment facilities. Incineration at high temperatures with appropriate emission controls is typically required. Never dispose of this substance through regular drains or waste streams. Consult local environmental authorities for specific disposal requirements and authorized waste management companies.

How to transport 2-(chloromethyl)oxirane?

2-(chloromethyl)oxirane is classified as UN Class 6.1 (toxic substances) Packing Group II for transportation purposes. It requires appropriate hazardous goods packaging, labeling with GHS pictograms (GHS02, GHS08, GHS06, GHS05), and proper shipping documentation. Transport vehicles must comply with ADR regulations for toxic substances. Only trained personnel should handle the transportation, and emergency response information must accompany shipments. Special routing and timing restrictions may apply in certain jurisdictions.

Is 2-(chloromethyl)oxirane subject to special regulations?

2-(chloromethyl)oxirane is subject to extensive regulatory oversight due to its Category 1B carcinogenic classification under CLP regulation. It requires registration under REACH for commercial use in Europe. The substance may be subject to authorization requirements and workplace exposure limits. Users must implement appropriate risk management measures and provide safety data sheets. Strict occupational health monitoring and reporting requirements apply to facilities handling this compound for commercial purposes.

Where to buy 2-(chloromethyl)oxirane in Europe?

2-(chloromethyl)oxirane is available through specialized chemical distributors like OYSI, which serves the European market with technical-grade chemicals. Due to its hazardous nature and regulatory requirements, procurement requires proper documentation, safety qualifications, and compliance with local regulations. OYSI can provide technical support, safety documentation, and appropriate packaging for professional users. Contact OYSI directly to discuss specific requirements, quantities, and regulatory compliance for your application.

Data Sources

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