This compound belongs to the class of organic compounds known as 1,3-dioxolanes. These are organic compounds containing 1,3-dioxolane, an aliphatic five-member ring with two oxygen atoms in ring positions 1 and 3.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No item‑specific application protocols (assays, immuno applications, etc.) are provided for this small‑molecule monomer. For laboratory deployment, consider the following general, non‑validated workflows:
Polymerization screening (general):
Degas monomer and solvent by nitrogen sparging (15–30 min). If inhibitor removal is performed, work cold and under inert gas.
Charge monomer, solvent, and initiator (e.g., AIBN 0.5 wt%) to a sealed vial; purge headspace; heat at 70 °C with stirring. Monitor conversion by 1H NMR (vinyl signal decay).
Thiol–ene coupling (general):
Combine 1.0 equiv 2‑vinyl‑1,3‑dioxolane with 1.0 equiv thiol, 1 wt% photoinitiator in EtOAc. Irradiate at 365–405 nm under N2 until vinyl signals disappear.
Metathesis functionalization (general):
Dry all reagents/solvents; add 2–3 mol% Hoveyda–Grubbs II, suitable olefin partner (1.5–2.0 equiv) in toluene at 40 °C; monitor by GC/NMR.
These are starting points only; conduct your own optimization and safety assessment before scale‑up.
Biological Roles
This product is intended for materials science and synthetic chemistry. No specific biological role is associated with 2‑vinyl‑1,3‑dioxolane.
General considerations (literature):
The 1,3‑dioxolane motif is common in protected carbohydrate chemistry and in some polymer backbones, but 2‑vinyl‑1,3‑dioxolane itself is not a natural metabolite.
In biochemical contexts, acetals are generally stable under neutral/basic aqueous conditions and cleave under acidic conditions; however, this compound is not used as a buffer or biochemical reagent.
Any toxicology, biodegradation, or ecotoxicity assessments should be derived from dedicated studies; consult SDS and environmental health literature. No clinical or therapeutic claims are made or implied.
For lab use only: If exposure to biological systems is intended (e.g., biomaterials R&D), perform application‑specific biocompatibility and extractables/leachables testing on the formulated polymer, not just the monomer.
Buffer Applications
Not typically applicable. 2‑Vinyl‑1,3‑dioxolane is a reactive monomer/building block and is not used as a buffering agent. For laboratory work involving this compound, refer instead to the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections.
Green Alternatives
Perspective: 2‑Vinyl‑1,3‑dioxolane is a functional monomer rather than a process solvent. Greenness is best considered in terms of synthesis route, solvent choices during use, and end‑of‑life of resulting polymers.
Potential greener choices and strategies (literature/general):
Alternative monomers:
Bio‑based vinyl ethers or allyl ethers derived from glycerol/isosorbide can provide similar reactivity with renewable feedstocks.
Allyl/itaconate esters may offer lower toxicity profiles and biodegradability in some copolymers.
Process solvent optimization:
Replace chlorinated solvents (e.g., DCM) with ethyl acetate, MeTHF, CPME, or dimethyl carbonate where compatible.
Use bulk or high‑solids formulations to minimize VOCs; consider reactive diluents to reduce solvent.
Catalysis:
Employ photo‑initiated or enzyme‑mediated processes at ambient temperature to reduce energy demand where feasible.
Trade‑offs:
Vinyl acetals can offer lower odor and potential toxicity than aromatics like styrene, but they may form peroxides and require inhibitors.
Bio‑based or green solvents may alter polymerization kinetics, inhibitor solubility, or cure speed; re‑optimize initiator systems and light intensity.
Mini comparison (general, non‑spec):
2‑Vinyl‑1,3‑dioxolane vs. styrene: less aromatic content, potentially milder odor; different Tg and reactivity ratios in copolymerizations.
2‑Vinyl‑1,3‑dioxolane vs. linear vinyl ethers: improved hydrolytic stability from the cyclic acetal, but possibly higher ring‑derived persistence in the environment—evaluate by LCA for your application.
Pharmaceutical Uses
No item‑specific pharmacopeial status or excipient grade is provided for this product; refer to CoA/Spec Sheet if required.
General, non‑clinical context:
Potential roles in pharmaceutical materials R&D include use as a comonomer or reactive diluent in UV/EB‑curable coatings, adhesive systems, or medical device coatings after proper biocompatibility assessment of the cured polymer.
The 1,3‑dioxolane motif can influence polymer polarity and glass transition temperature, enabling tack and barrier tuning in pressure‑sensitive adhesives and coatings.
If considering for GMP‑adjacent work, ensure qualification of: monomer purity (residual inhibitors), residual monomer content in the polymer, extractables/leachables, and compliance with relevant standards (e.g., ISO 10993 for devices). No therapeutic or clinical claims are made.
Note: This listing is for research use only.
Physical Properties
Item‑specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical properties for 2‑vinyl‑1,3‑dioxolane (for reference only; not product specifications):
Molecular formula (literature): C5H8O2
Molecular weight (literature): ~100.12 g·mol⁻¹
Physical state: typically a colorless, flammable liquid with an ether‑like odor.
Volatility: moderate; lower than 1,3‑dioxolane and higher than larger vinyl acetals.
Solubility: expected miscibility with common organic solvents (ethers, esters, hydrocarbons); water solubility likely moderate to low compared with 1,3‑dioxolane due to the vinyl substituent.
Refractive index, density, BP/MP, logP, pKa: Specific values vary by source and are not stated here. Consult primary data sources or the item’s CoA for exact numbers.
General chemistry notes:
The vinyl group enables radical, cationic, and metathesis chemistry; the cyclic acetal is relatively stable under neutral/basic conditions but labile to strong acids (especially aqueous).
As with many vinyl ethers/acetals, peroxide formation and autoxidation can occur on prolonged air exposure; verify before distillation (peroxide test strips) and consider stabilizers.
Always rely on the product’s CoA/SDS for authoritative physical data and handling limits.
Quality and Grades
Item‑specific quality details (grade, purity, stabilizer/inhibitor, metal/UV/peroxide limits): Not specified for this item; refer to CoA/Spec Sheet.
Context and interpretation for professional use:
Research grade vs. inhibitor content: Vinyl acetals/ethers are often supplied with small amounts of polymerization inhibitors (e.g., MEHQ, BHT, hydroquinone, or acid scavengers). Presence/amount of inhibitor affects polymerization kinetics and radical scavenging; confirm by CoA if you require inhibitor‑free monomer.
Low‑UV/HPLC grade: Where chromatography compatibility is important (e.g., photopolymer formulations), low‑UV absorbance specifications may be requested. If needed, verify absorbance at relevant wavelengths on the CoA.
Peroxide specification: For distillation or sensitive polymerizations, some users require a maximum peroxide value. If this parameter matters in your workflow, request or measure it upon receipt.
Trace metals/ions: Generally less critical for free‑radical polymerizations but can be important for metathesis (Ru catalysts) or coordination catalysis; inquire about metal content if using with sensitive catalysts.
Batch consistency: Viscosity and inhibitor level can drift with storage; record lot numbers and date of opening. If highly reproducible polymerization behavior is needed, consider inhibitor removal/standardization and pre‑titration of initiator.
Documentation: Aladdin Scientific recommends consulting the lot‑specific CoA and SDS for definitive values and any special release testing performed for this SKU.
Reaction and Applications
Use domains (literature/general):
Radical polymerization: Homopolymerization and copolymerization with acrylates, maleic anhydride, vinyl ethers, or styrenics to give acetal‑containing materials. The cyclic acetal imparts polarity, adhesion, and chemical resistance. Control inhibitor content prior to polymerization.
Cationic polymerization/UV curing: Under photoacid or strong Brønsted acids, vinyl acetals can undergo cationic polymerization. Useful in coatings and photoresists; moisture control is critical to avoid acetal cleavage.
Click‑type additions to alkene: Thiol–ene additions under radical initiation afford β‑thioether acetals; often efficient under UV/thermal peroxide initiation.
Metathesis chemistry: Terminal vinyl group participates in cross‑metathesis and ring‑closing metathesis (RCM with suitable partners), enabling late‑stage incorporation of the 1,3‑dioxolane motif.
Oxidation/epoxidation: Prilezhaev epoxidation of the vinyl double bond, dihydroxylation (e.g., OsO4/NMO), hydroboration–oxidation to yield primary alcohol sidechains tethered to the dioxolane ring.
Functional handle for protection strategies: The 1,3‑dioxolane ring can serve as an acetal protecting group environment; while this compound is not a protecting reagent per se, its motif is compatible with many protecting‑group strategies.
Practical tips:
Inhibitor management: If supplied inhibited, pass through a short plug of basic alumina or wash with dilute NaOH (organic phase dried) to remove phenolic inhibitors; verify by UV or spiking studies. Beware that removing inhibitor increases polymerization hazard—work cold and under inert gas.
Moisture/acid sensitivity: Maintain anhydrous conditions and avoid strong acids to preserve the acetal ring.
Scale‑up: Exothermic polymerizations demand calorimetry and staged initiator feeds; consider solution polymerization to moderate viscosity.
Reaction Conditions
General (literature‑based, not item‑specific specifications):
UV: 365–405 nm; seconds to minutes exposure; N2 blanket recommended.
Olefin metathesis (cross‑metathesis):
Catalysts: Grubbs/Hoveyda–Grubbs (0.5–5 mol%).
Solvents: DCM, toluene, or green alternatives (CPME/MeTHF) if catalyst‑compatible.
Temperature: 20–60 °C; time: 1–12 h.
Considerations: residual inhibitor or protic impurities can suppress catalyst activity; pass through alumina if needed.
Oxidations of the vinyl group:
Epoxidation: mCPBA (1.1–1.5 equiv) in DCM, 0–25 °C.
Dihydroxylation: OsO4 (cat.)/NMO in t‑BuOH/H2O, 0–25 °C.
Hydroboration–oxidation: BH3·THF then H2O2/NaOH, 0–25 °C.
All parameters above are representative literature ranges; optimize for your specific substrate set and scale.
Safety and Handling
Item‑specific hazard information:
GHS/CLP classification, pictograms, signal word, H‑statements: Not specified for this item; refer to SDS.
General safety guidance for vinyl acetals/ethers (literature/industry practice):
Likely hazards: flammable liquid and vapor; may form explosive peroxides upon storage in air/oxygen; may undergo hazardous polymerization if uninhibited and heated or exposed to radical sources.
PPE: chemical‑resistant gloves (e.g., nitrile), splash goggles, lab coat; use in a functioning fume hood.
Incompatibilities: strong acids (promote acetal cleavage/cationic polymerization), strong oxidizers, radical initiators, peroxides; avoid contact with peroxidizing agents and acid chlorides in the presence of moisture.
Handling: minimize exposure to air and light; purge headspace with inert gas (N2/Ar) after each use. If inhibitor content is unknown, handle as an uninhibited monomer; keep cold.
Peroxide risk: test stored material periodically before concentration or distillation; if peroxides are detected above safe limits, dispose per institutional procedures.
Fire safety: keep away from heat/sparks/open flames; use CO2, dry chemical, or foam for small fires; water spray for cooling containers.
First aid (overview; consult SDS for details):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product’s SDS for definitive hazard classifications, exposure limits, and emergency procedures.
Solvent Selection
This product is primarily a reactive monomer/building block rather than a routine process solvent. Solvent selection is therefore usually discussed in the context of its use in reactions or polymerizations.
General guidance (literature/experience):
Polarity class: moderately polar aprotic (cyclic acetal/ether). It dissolves well in common organic media used for radical/cationic polymerizations and alkene transformations.
Typical compatible solvents: toluene, ethyl acetate, MTBE/diethyl ether, THF/2‑MeTHF, acetonitrile, dichloromethane. Choose based on reaction mechanism (radical vs cationic) and catalyst solubility.
Water: vinyl acetals are susceptible to acid‑catalyzed hydrolysis; avoid aqueous strong acids. Neutral aqueous systems may still lead to slow hydrolysis; use dry conditions when acetal integrity is required.
When to use neat (bulk polymerization): neat monomer enables higher productivity but elevates exotherm and gel risk; ensure efficient heat removal and inhibitor control.
Quick comparison (general):
Versus vinyl ethers: similar reactivity; the cyclic acetal offers increased hydrolytic stability vs linear vinyl ethers.
Versus styrene: typically lower toxicity/odor and different glass transition when copolymerized; less resonance stabilization of radical, affecting copolymerization parameters.
Note: For highly sensitive catalysis (e.g., olefin metathesis), select rigorously dried, inhibitor‑compatible solvents and verify that residual inhibitor in the monomer does not poison the catalyst.
Storage and Reconstitution
Item‑specific instructions:
Storage conditions (from Product Data): Store at 2–8 °C.
Shipping: Shipped on wet ice.
General guidance for this class of materials (vinyl acetals/ethers):
Atmosphere: Store under inert gas (N2/Ar) in tightly sealed, amber glass to minimize oxidation, light exposure, and inhibitor degradation.
Inhibitor: Presence/type and concentration are Not specified for this item; refer to CoA/Spec Sheet. If inhibitor levels are critical for your process, verify upon receipt and before use.
Stability: Avoid strong acids and moisture to prevent acetal cleavage. Keep away from heat and sources of radical initiation.
After opening: Record the open date; re‑blanket headspace with nitrogen; return promptly to 2–8 °C. Periodically test for peroxides before any concentration or distillation.
Long‑term storage: For extended storage, small aliquots under inert gas at 2–8 °C are recommended to reduce headspace oxygen and repeated thermal cycling.
Reconstitution: Not applicable; supplied as a neat liquid monomer (no reconstitution required). If solidification or phase separation is observed at low temperature, allow to equilibrate to room temperature under inert gas and mix thoroughly before use.
Always consult the lot‑specific CoA and SDS for definitive storage constraints and stability information.
Structure and Identity
Brief description: 2‑Vinyl‑1,3‑dioxolane is a five‑membered 1,3‑dioxolane ring bearing a vinyl substituent at the acetal (2‑) position; it is a vinyl acetal/ether‑like monomer and protecting‑group motif.
Product Data (item‑specific):
SKU: V472440
Product name: 2‑Vinyl‑1,3‑dioxolane
CAS: 3984‑22‑3
InChIKey: 182113 (as provided in Product Data)
Storage: 2–8 °C; shipped on wet ice
Research use: For research use only
Literature/computed identifiers (for reference only; not item specification):
The 2‑substituted acetal center is prochiral in many representations; the ring oxygens are equivalent by symmetry in the parent, and vinyl substitution does not typically render a stable stereocenter.
2D description: A 1,3‑dioxolane ring (–O–CH2–CH2–O–) whose central carbon (between the two oxygens) carries a –CH=CH2 substituent.
Notes:
Where exact identifiers for this catalog item are needed (e.g., canonical SMILES, definitive InChIKey), please refer to the product’s CoA/Spec Sheet or SDS.
Synthetic Utility
Key functional elements:
Terminal alkene (vinyl): amenable to radical additions (thiol–ene), hydrofunctionalizations (hydroboration–oxidation, hydrosilylation), epoxidation/dihydroxylation, ozonolysis/oxidative cleavage, and olefin metathesis.
Cyclic acetal (1,3‑dioxolane): stable under neutral and basic conditions, cleaved by aqueous acids; serves as a masked carbonyl environment that survives many transformations on the alkene.
Typical transformations (literature/general):
Cross‑metathesis with terminal/internal alkenes to install diverse substituents while retaining the dioxolane ring.
Radical copolymerization with acrylates or maleimides to create polar copolymers; the acetal ring contributes to adhesion and solvent resistance.
Electrophilic additions under cationic conditions (photoacid/Brønsted acid) to yield poly(ketal/ether) networks.
Oxidative elaboration of the vinyl to alcohols/diols, followed by selective acetal hydrolysis to reveal carbonyl handles for further derivatization.
Retrosynthetic value:
The 2‑substituted dioxolane can be traced back to acetalization of carbonyl compounds (e.g., formation of dioxolanes from aldehydes/ketones with ethylene glycol), followed by introduction of the vinyl group via Wittig/HWE, Tebbe/Peterson, or elimination strategies.
Practical notes:
Maintain anhydrous, acid‑free conditions to preserve the acetal during transformations.
If performing polymerizations, quantify inhibitor content and oxygen levels; oxygen scavenging may be required for controlled radical methods (RAFT/ATRP variants).
Target Specificity
Not applicable. This product is a small‑molecule monomer/building block and does not have biological target specificity (no antigen/epitope, clone, or isotype). For practical use cases, refer to Reaction & Applications and Synthetic Utility.
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