5-Methyl-3-vinyloxazolidin-2-one
[CAS# 3395-98-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 5-Methyl-3-vinyloxazolidin-2-one
• Synonyms: 3-ethenyl-5-methyl-1,3-oxazolidin-2-one
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.14
• CAS Registry Number: 3395-98-0
• EC Number: 809-852-5
• SMILES: CC1CN(C(=O)O1)C=C

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

5-Methyl-3-vinyloxazolidin-2-one is a heterocyclic organic compound belonging to the class of oxazolidinones, characterized by a five-membered ring containing both oxygen and nitrogen atoms. In this compound, the ring structure is modified with a methyl group at the 5-position and a vinyl group at the 3-position, while a carbonyl group is present at the 2-position, forming the oxazolidin-2-one core.

The oxazolidinone ring system has played a significant role in organic synthesis and medicinal chemistry, where it serves as both a synthetic intermediate and a pharmacophore. The specific substitution pattern of 5-methyl-3-vinyloxazolidin-2-one imparts particular interest because the vinyl group offers a reactive site for further chemical transformations, such as polymerization or addition reactions, and the 5-methyl group influences the steric and electronic environment of the ring.

The compound can be synthesized through multiple pathways, one of which involves the cyclization of an appropriately substituted amino alcohol precursor with a carbonyl-containing compound. Alternatively, ring formation may proceed via an intramolecular nucleophilic substitution followed by functionalization at the nitrogen atom. The introduction of the vinyl group is often achieved through alkylation or elimination reactions, while the methyl group is generally introduced via selective substitution prior to ring closure.

From a chemical perspective, 5-methyl-3-vinyloxazolidin-2-one is typically a crystalline solid or viscous liquid, depending on the purity and temperature. It has moderate solubility in common organic solvents such as dichloromethane, tetrahydrofuran, and ethyl acetate. The presence of the vinyl group introduces a region of unsaturation that is reactive toward electrophiles and radical species, enabling this compound to serve as a monomer or reactive intermediate in the synthesis of more complex molecules.

This compound has found application in synthetic organic chemistry as a chiral auxiliary or reagent in stereoselective reactions. Although 5-methyl-3-vinyloxazolidin-2-one itself is not chiral, analogs with chiral centers at the 4- or 5-positions have been developed for asymmetric synthesis. The vinyl group is particularly useful for constructing side chains or cyclic structures via cycloaddition reactions, including Diels-Alder and \[2+2] cycloadditions.

In polymer chemistry, oxazolidinone derivatives with vinyl substituents are used as monomers in the synthesis of specialty polymers. Radical polymerization of the vinyl group allows for the preparation of polymers with pendant oxazolidinone rings, which may impart unique thermal, mechanical, or solubility properties to the resulting materials. These polymers can be used in coatings, adhesives, or biomedical applications depending on their structure and formulation.

Analytical characterization of 5-methyl-3-vinyloxazolidin-2-one includes nuclear magnetic resonance (NMR) spectroscopy to confirm the presence of the vinyl and methyl substituents, infrared (IR) spectroscopy for identifying the carbonyl stretch of the lactam group, and mass spectrometry for molecular weight verification. Its structure can also be confirmed using single-crystal X-ray diffraction when crystalline samples are available.

Safety data for this compound are limited in the open literature. However, compounds containing oxazolidinone rings and reactive alkenes should be handled with appropriate laboratory precautions, including the use of gloves, eye protection, and proper ventilation. The vinyl group may undergo polymerization upon exposure to heat or light, and standard stabilizers may be added to prevent this during storage.

In summary, 5-methyl-3-vinyloxazolidin-2-one is a functionalized oxazolidinone of interest in synthetic organic and polymer chemistry due to its reactive vinyl group and stable heterocyclic core. It serves as a versatile intermediate for the synthesis of more complex structures and materials with potential utility in industrial and research applications.

References

2020. Ruthenium-Catalyzed Synthesis of Vinylamides. Synfacts, 16(6).
DOI: 10.1055/s-0040-1707845

Compound: 2-Oxazolidinone, 3-ethenyl-5-methyl-, homopolymer.
URL: https://www.epa.gov/tsca-inventory