2-(chloromethyl)oxirane
C3H5ClO
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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 chlorinated epoxide compound with high reactivity and significant industrial applications as a chemical intermediate. This three-membered ring compound, also known by its EC number 203-439-8, represents a critical building block in organic synthesis and polymer chemistry. With a molecular formula of C3H5ClO and molecular weight of 92.52 g/mol, 2-(chloromethyl)oxirane combines the reactive characteristics of both epoxide and chloromethyl functional groups, making it exceptionally valuable for cross-linking reactions and chain extension processes. The compound exhibits significant safety considerations due to its classification profile, including flammable liquid category 3, carcinogenicity category 1B, and acute toxicity category 3 across multiple exposure routes. Its corrosive properties toward skin (category 1B) and skin sensitization potential require strict handling protocols and appropriate personal protective equipment. The ADR classification of 6.1 reflects its toxic nature during transportation, necessitating specialized logistics arrangements. In industrial applications, 2-(chloromethyl)oxirane serves primarily as a reactive intermediate in epoxy resin formulations, where it functions as a cross-linking agent to enhance mechanical properties and chemical resistance. It also finds application in the synthesis of specialty polymers and as a building block for pharmaceutical intermediates. Unlike simpler compounds such as aziridine, this chlorinated epoxide offers dual functionality that enables more complex chemical modifications. The compound's bifunctional nature allows for controlled polymerization reactions and the introduction of chlorine-containing side chains, making it particularly valuable in developing flame-retardant materials and specialized coatings. OYSI maintains reliable supply chains for 2-(chloromethyl)oxirane to support European industrial customers requiring this specialized chemical intermediate.
Safety & Classification
Flam. Liq. 3; Carc. 1B; Acute Tox. 3 *; Acute Tox. 3 *; Acute Tox. 3 *; Skin Corr. 1B; Skin Sens. 1
GHS Pictograms
Flame
GHS02
Flammable. May ignite on contact with air, water, or heat sources.
Health Hazard
GHS08
Serious health hazard. May cause cancer, organ damage, or genetic defects.
Skull and Crossbones
GHS06
Acute toxicity. Fatal if swallowed, in contact with skin, or if inhaled.
Corrosion
GHS05
Corrosive. Causes severe skin burns and eye damage.
HHazard Statements (H-Statements)
Describe the nature and severity of the hazard
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
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
Measures if substance contacts the skin
Eye Contact
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
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 Number | 2023 |
| ADR Class | 6.1 |
| Packing Group | II |
| Tunnel Code | D/E |
| Proper Shipping Name | Epichlorhydrin |
| Marine Pollutant | No |
Frequently Asked Questions
What is 2-(chloromethyl)oxirane?
2-(chloromethyl)oxirane is an organochlorine epoxide 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 highly reactive. With a molecular weight of 92.52 g/mol, it is classified as a dangerous substance due to its carcinogenic, toxic, corrosive, and flammable properties. It is widely recognized as an important industrial intermediate in chemical synthesis.
What are the physicochemical properties of 2-(chloromethyl)oxirane?
2-(chloromethyl)oxirane is a colorless liquid at room temperature with a characteristic sweet, ether-like odor. It has high reactivity due to the presence of both epoxide and chloromethyl functional groups. The compound is miscible with most organic solvents and has limited solubility in water. It exhibits flammable properties and is volatile at ambient temperatures, requiring careful handling due to its tendency to undergo ring-opening reactions.
What is 2-(chloromethyl)oxirane used for?
2-(chloromethyl)oxirane serves primarily as a chemical intermediate in the production of various industrial compounds. It is used in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. The compound acts as a cross-linking agent and is utilized in the production of epoxy resins, ion-exchange resins, and other polymer materials. Its dual functionality makes it valuable for creating complex molecular structures in organic synthesis applications.
How to handle 2-(chloromethyl)oxirane safely?
2-(chloromethyl)oxirane requires strict safety measures including chemical-resistant gloves, protective clothing, and respiratory protection in well-ventilated areas. Personnel must wear safety goggles and work in fume hoods to prevent inhalation exposure. Due to its carcinogenic and corrosive nature, skin and eye contact must be completely avoided. Emergency eyewash stations and safety showers should be readily accessible, and only trained personnel should handle this substance.
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 sources. Storage temperature should be kept below 25°C to minimize vapor formation. The substance should be separated from strong bases, acids, and nucleophiles due to its reactive nature. Storage areas must comply with regulations for flammable and toxic substances, with appropriate fire suppression systems installed.
What to do in case of contact with 2-(chloromethyl)oxirane?
Immediate action is required for any contact with 2-(chloromethyl)oxirane. For skin contact, remove contaminated clothing and wash affected area with plenty of water for at least 15 minutes. In case of eye contact, rinse immediately with water for 15-20 minutes and remove contact lenses if present. For inhalation, move the person to fresh air immediately. Seek medical attention promptly in all cases due to the substance's toxic and corrosive properties.
How to dispose of 2-(chloromethyl)oxirane properly?
2-(chloromethyl)oxirane must be disposed of as hazardous waste through licensed waste management companies specializing in toxic and carcinogenic substances. The waste cannot be discharged into sewers, waterways, or regular waste streams. Incineration at high temperatures in specialized facilities is typically required. All disposal activities must comply with local environmental regulations and waste classification codes, with proper documentation and tracking throughout the disposal process.
How to transport 2-(chloromethyl)oxirane?
2-(chloromethyl)oxirane is classified under ADR Class 6.1 (toxic substances) Packing Group II, requiring specialized transport procedures for dangerous goods. Transport must use UN-approved packaging and proper labeling with toxic substance markings. Drivers require ADR certification and vehicles must carry appropriate emergency equipment. Transport documents must include safety data sheets and emergency response information, and shipments must comply with routing restrictions for toxic materials.
Is 2-(chloromethyl)oxirane subject to specific regulations?
2-(chloromethyl)oxirane is subject to extensive regulations under REACH, CLP, and national chemical safety frameworks due to its carcinogenic classification (Category 1B). Users must comply with occupational exposure limits, worker protection requirements, and environmental discharge restrictions. The substance requires safety data sheets, hazard communication, and may be subject to authorization or restriction procedures. Industrial users must implement risk management measures and report usage under chemical inventory regulations.
Where to buy 2-(chloromethyl)oxirane in Europe?
2-(chloromethyl)oxirane is available through OYSI, a specialized European distributor of technical chemicals serving industrial customers across the continent. OYSI provides regulatory compliance support, technical documentation, and logistics services for hazardous chemicals. Due to the substance's dangerous properties and regulatory requirements, procurement requires proper business credentials, safety assessments, and compliance with local handling regulations. Contact OYSI directly for availability, specifications, and regulatory guidance.
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Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.