Description

Vinylene Carbonate (CAS 872-36-6) is a high-purity, cyclic carbonate compound with the molecular formula C₃H₂O₃, also known by its IUPAC name 1,3-dioxol-2-one. This colorless to pale-yellow liquid is a critical electrolyte additive in advanced lithium-ion battery systems, renowned for its ability to enhance anode stability and cycle life. Its unique vinylene group enables polymerization on electrode surfaces, forming a robust solid-electrolyte interphase (SEI) layer that minimizes electrolyte decomposition and improves high-temperature performance. Vinylene carbonate is synthesized under stringent quality controls to ensure >99% purity, making it ideal for research and industrial applications in energy storage. Packaged under inert gas to prevent moisture absorption, it is compatible with organic solvents such as ethylene carbonate (EC) and dimethyl carbonate (DMC).

Properties

• CAS Number: 872-36-6
• Complexity: 84.2
• IUPAC Name: 1,3-dioxol-2-one
• InChI: InChI=1S/C3H2O3/c4-3-5-1-2-6-3/h1-2H
• InChI Key: VAYTZRYEBVHVLE-UHFFFAOYSA-N
• Exact Mass: 86.000393922
• Molecular Formula: C3H2O3
• Molecular Weight: 86.05
• SMILES: C1=COC(=O)O1
• Topological: 35.5
• Monoisotopic Mass: 86.000393922
• Physical Description: Other Solid; Liquid
• Synonyms: VINYLENE CARBONATE, 1,3-Dioxol-2-one, 872-36-6, Vinyl carbonate, Carbonic acid, cyclic vinylene ester, 1X0ZZF9WFV, EINECS 212-825-5, NSC 20980, NSC 47201, vinylidene carbonate, BRN 0105683, NSC-20980, NSC-47201, DTXSID1074888, EC 212-825-5, LBG-84922, CYCLIC VINYLENE ESTER CARBONIC ACID, 1,3-Dioxol-2-one (9CI), DTXCID8048573, 212-825-5, MFCD00005380, 2H-1,3-dioxol-2-one, Vinylene carbonate (stabilized with BHT), WLN: T5OVOJ, Vinylene Carbonate (Contains Up to 2% BHT), C3H2O3, starbld0011148, UNII-1X0ZZF9WFV, SCHEMBL35245, SCHEMBL992934, SCHEMBL15049055, VAYTZRYEBVHVLE-UHFFFAOYSA-, Carbonic acid, cyclicvinylene ester, NSC20980, NSC47201, BBL027517, STL373475, AKOS015855830, CS-W013752, SB66334, SY001314, DB-056985, NS00005704, V0015, Vinylene carbonate, purum, >=97.0% (GC), EN300-120679, A842047, Q2802973, InChI=1/C3H2O3/c4-3-5-1-2-6-3/h1-2H, Vinylene carbonate, contains <=2% BHT as stabilizer, 97%, Vinylene carbonate, 99.5%, acid <200 ppm, H2O <100 ppm, Vinylene carbonate, contains 80 ppm BHT as stabilizer, 99%, 25747-73-3

Application

Vinylene carbonate is a pivotal additive in lithium-ion battery electrolytes, where it polymerizes on anode surfaces (e.g., graphite or silicon) to form a stable SEI layer, reducing irreversible capacity loss. It significantly improves high-temperature performance by suppressing gas generation and electrolyte degradation. Researchers also utilize it to passivate silicon-based anodes, mitigating volume expansion issues. Its applications extend to next-generation batteries, including lithium-sulfur and solid-state systems.

Safety and Hazards

GHS Hazard Statements

• H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
• H311 (92.8%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H315 (98.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H317 (97.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
• H318 (97%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H361 (14.4%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
• H373 (92.8%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
• H411 (97%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P203, P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P391, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (99.2%)
• Acute Tox. 3 (92.8%)
• Skin Irrit. 2 (98.9%)
• Skin Sens. 1 (97.3%)
• Eye Dam. 1 (97%)
• Repr. 2 (14.4%)
• STOT RE 2 (92.8%)
• Aquatic Chronic 2 (97%)

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