5-Methyl-3-vinyloxazolidin-2-one CAS No. 3395-98-0

Uses

• Synthetic Intermediate: Used in asymmetric synthesis (as chiral auxiliaries) or as drug discovery scaffolds.

• Pharmaceutical Relevance: Related oxazolidinones (like linezolid) are known antibiotics, but this specific derivative is more likely a research chemical or synthetic building block.

• Adhesives: Used as a reactive diluent in UV-cured adhesives, contributing excellent adhesion properties on common substrates even at low dosages.

• Coatings: Used as a reactive diluent in UV-cured coatings, enhancing toughness and resistance properties of a cured film.

• Inks: Used in UV-curing inks for digital UV printing and 3D printing, improving adhesion on low-energy surfaces and mechanical properties.

• Molecular Formula: C₆H₉NO₂

• Molecular Weight: 127.14 g/mol

• IUPAC Name: 3-ethenyl-5-methyl-1,3-oxazolidin-2-one

• Compound Class: Oxazolidinone derivative (a five-membered heterocycle containing oxygen, nitrogen, and a carbonyl group)

• Core Structure: Oxazolidin-2-one (a five-membered cyclic carbamate)

• Substituents:

  • Vinyl group at the 3-position (–CH=CH₂)

  • Methyl group at the 5-position

• Functional Groups:

  • Lactam (cyclic carbamate)

  • Vinyl group (alkene)

  • Methyl substituent

• Reactivity:

  • The vinyl group makes it reactive in polymerization or addition reactions.

  • The oxazolidinone ring is relatively stable but can undergo nucleophilic attack at the carbonyl.

• Chirality: Potential chirality at C5 if stereochemistry is specified

Safety and Hazards

• Hazard Classification:

  • Acute toxicity (oral), Category 4 (H302)

  • Skin corrosion/irritation, Category 2 (H315)

  • Serious eye damage/eye irritation, Category 1 (H318)

  • Skin sensitisation, Category 1 (H317)

  • Specific target organ toxicity – Single exposure, Category 3 (H335)

  • Hazardous to the aquatic environment – Chronic Hazard, Category 2 (H411)

• Label Elements:

  • Signal word: Danger

  • Pictograms: GHS05, GHS07, GHS09

  • Precautionary Statements:

    • P261: Avoid breathing fume, mist, spray, vapours.

    • P264: Wash hands thoroughly after handling.

    • P273: Avoid release to the environment.

    • P280: Wear eye protection, protective clothing, protective gloves.

    • P301+P312: IF SWALLOWED: Call doctor if you feel unwell.

    • P302+P352: IF ON SKIN: Wash with plenty of soap and water.

    • P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.

    • P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

    • P310: Immediately call a doctor.

    • P312: Call doctor if you feel unwell.

    • P333+P313: If skin irritation or rash occurs: Get medical advice/attention.

    • P391: Collect spillage.

    • P403+P233: Store in a well-ventilated place. Keep container tightly closed.

    • P405: Store locked up.

    • P501: Dispose of contents and container to hazardous or special waste collection point, in accordance with local, regional, national, and/or international regulation.

Environmental Considerations

• Persistence and Degradability: Not readily biodegradable.

• Bioaccumulative Potential: Does not significantly accumulate in organisms.

• Mobility in Soil: The substance will not evaporate into the atmosphere from the water surface. Adsorption to solid soil phase is not significant.

• Ecotoxicity: Toxic to aquatic life with long-lasting effects.

Regulatory Information

• Regulations: Subject to various regulations including the Control of Major Accident Hazards Regulations (COMAH) and the Control of Substances Hazardous to Health Regulations (COSHH) in the UK.

• Transport Information: Classified as UN3082, Environmentally hazardous substance, liquid, n.o.s., Packing Group III, with environmental hazards noted.

Product Documents

• Safety Data Sheet (SDS)
• Certificate of Analysis
• Product Brochure
• Technical Data Sheet