4-Chloro-1,3-dioxolan-2-one: Properties, Uses & FAQs

4-Chloro-1,3-dioxolan-2-one is a halogenated cyclic carbonate compound used as a reactive intermediate and specialty additive in organic synthesis and electrochemical research.

IUPAC Name

4-Chloro-1,3-dioxolan-2-one

Common Synonym

Chloroethylene carbonate; 4-Chloro-1,3-dioxolan-2-one

Molecular Formula

C3H3ClO3

Molecular Weight

122.50 g/mol

Product SKU

C154009

Functional Class

Halogenated cyclic carbonate

Key Applications

Organic synthesis intermediate; lithium-ion battery electrolyte additive research

What Is 4-Chloro-1,3-dioxolan-2-one?

4-Chloro-1,3-dioxolan-2-one (also called chloroethylene carbonate) is a five-membered cyclic carbonate bearing a chlorine substituent at the 4-position of the dioxolane ring. Its molecular formula is C₃H₃ClO₃ and its molecular weight is approximately 122.50 g/mol. The compound belongs to the class of halogenated cyclic carbonates, which are valued in organic chemistry for their electrophilic carbonyl character and ring-strain-assisted reactivity. The chlorine atom at the 4-position significantly increases the electrophilicity of the carbonyl centre compared with unsubstituted ethylene carbonate, making this reagent a versatile building block and reactive intermediate.

Chemical Properties and Reactivity

4-Chloro-1,3-dioxolan-2-one is a liquid or low-melting solid at room temperature with a characteristic ester-like odour. The compound is moisture-sensitive; contact with water or protic solvents leads to hydrolysis of the cyclic carbonate ring, generating chloroacetaldehyde and carbon dioxide as by-products alongside chlorohydrin-type intermediates. The reactive chlorine and electrophilic carbonyl make it susceptible to nucleophilic attack by amines, alcohols, and thiolates, enabling ring-opening reactions useful in polymer chemistry and medicinal chemistry synthesis. It should be handled under anhydrous, inert-atmosphere conditions to preserve reagent integrity.

The compound also exhibits relevance in electrochemical contexts: chlorinated ethylene carbonates have been investigated as film-forming electrolyte additives for lithium-ion batteries, where reductive decomposition at the anode surface is believed to contribute to solid electrolyte interphase (SEI) formation.

Storage, Handling and Safety

Due to its moisture sensitivity and potential corrosive and irritant properties, 4-Chloro-1,3-dioxolan-2-one must be stored in a tightly sealed container under dry, inert gas (nitrogen or argon) at cool temperatures (typically 2–8 °C or as specified on the product label). Researchers should consult the Safety Data Sheet (SDS) supplied with product SKU C154009 before use. Standard laboratory personal protective equipment—including chemical-resistant gloves, safety goggles, and a laboratory coat—should be worn. Work should be conducted in a well-ventilated fume hood. In the event of skin or eye contact, flush immediately with copious water and seek medical advice. Incompatible materials include strong bases, strong oxidisers, and water.

Research Applications

4-Chloro-1,3-dioxolan-2-one serves multiple roles in modern research:

• Organic synthesis: As a halogenated cyclic carbonate, it acts as an electrophilic carbonylating and chloroalkylating agent. Ring-opening with nucleophiles provides access to β-chloro carbonate and carbamate derivatives.
• Polymer chemistry: Cyclic carbonates are established monomers or co-monomers in ring-opening polymerisation (ROP); the chlorine functionality can be used for post-polymerisation modification.
• Battery research: Chlorinated ethylene carbonate derivatives have been explored as electrolyte additives to improve SEI quality and cycle life of lithium-ion and lithium-metal batteries.
• Medicinal chemistry: The compound may serve as a synthon for introducing carbonate-linked or chlorohydrin-type moieties into drug candidates.

Researchers are advised to conduct a thorough literature search for the most current applications relevant to their specific synthetic targets.

Ordering and Specifications

4-Chloro-1,3-dioxolan-2-one is available from Aladdin Scientific under SKU C154009. When ordering, researchers should confirm the required purity grade, pack size, and any special packaging needs (e.g., ampouled under inert gas) with the Aladdin Scientific sales team. For bulk quantities or custom purity specifications, please contact our technical sales representatives. Current pricing, available pack sizes, and stock status can be found on the Aladdin Scientific product page for C154009. All products are subject to Aladdin's standard quality control procedures and are accompanied by a certificate of analysis (CoA) and SDS upon request.

Frequently asked questions

What is 4-Chloro-1,3-dioxolan-2-one used for in organic synthesis?

4-Chloro-1,3-dioxolan-2-one functions as a halogenated cyclic carbonate electrophile, enabling ring-opening reactions with amines, alcohols, and other nucleophiles to generate β-chloro carbamate and carbonate derivatives. It is also investigated as an electrolyte additive in lithium-ion battery research. Researchers should consult current literature for the latest synthetic applications.

How should 4-Chloro-1,3-dioxolan-2-one be stored to maintain stability?

The compound is moisture-sensitive and should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at cool temperatures (typically 2–8 °C). Exposure to water, protic solvents, strong bases, or strong oxidisers should be avoided. Always refer to the SDS for SKU C154009 for precise storage instructions.

Is 4-Chloro-1,3-dioxolan-2-one the same as chloroethylene carbonate?

Yes, 4-Chloro-1,3-dioxolan-2-one is commonly referred to as chloroethylene carbonate in the scientific literature. Both names describe the same five-membered cyclic carbonate structure with a chlorine substituent at the 4-position. When searching databases or literature, using both names or the molecular formula C3H3ClO3 will help ensure comprehensive results.

What safety precautions are required when handling 4-Chloro-1,3-dioxolan-2-one?

Researchers must wear appropriate PPE including chemical-resistant gloves, safety goggles, and a lab coat, and work inside a fume hood. The compound may be corrosive or irritating to skin, eyes, and the respiratory tract. The SDS provided with product C154009 must be reviewed before first use, and all local institutional safety regulations must be followed.

How can I order 4-Chloro-1,3-dioxolan-2-one from Aladdin Scientific?

4-Chloro-1,3-dioxolan-2-one is listed under SKU C154009 on the Aladdin Scientific website, where current pricing, pack sizes, and stock availability can be confirmed. For bulk orders, custom specifications, or additional technical information, please contact the Aladdin Scientific sales or technical support team directly.

References

1. Haynes, W.M. (Ed.). CRC Handbook of Chemistry and Physics. CRC Press. (General reference for cyclic carbonate chemistry and physical properties.)
2. Xu, K. Nonaqueous Liquid Electrolytes for Lithium-Based Rechargeable Batteries. Chemical Reviews, 2004, 104(10), 4303–4417. (Background on halogenated carbonate electrolyte additives.) doi:10.1021/cr030203g
3. Rokicki, G. Aliphatic Cyclic Carbonates and Spiroorthocarbonates as Monomers. Progress in Polymer Science, 2000, 25(2), 259–342. (Reference for cyclic carbonate ring-opening reactivity and applications in polymer chemistry.) doi:10.1016/S0079-6700(00)00006-X

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.