Bis(2-methoxyethyl) carbonate
[CAS# 626-84-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Bis(2-methoxyethyl) carbonate
• Synonyms: Carbonic Acid Bis(2-Methoxyethyl) Ester; Nsc 7314; Ethanol, 2-Methoxy-, Carbonate (2:1) (9Ci)
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.18
• CAS Registry Number: 626-84-6
• EC Number: 633-105-0
• SMILES: COCCOC(=O)OCCOC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.412, Calc.^*
• Boiling Point: 231.0 °C (760 mmHg), Calc.^*
• Flash Point: 85.7±20.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H319-H335-H360
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Bis(2-methoxyethyl) carbonate is an organic carbonate ester with the molecular formula C6H12O5. It is derived from carbonic acid and 2-methoxyethanol, a glycol ether. The structure consists of two 2-methoxyethyl groups bonded to a central carbonate functional group, making it a dialkyl carbonate.

The synthesis of bis(2-methoxyethyl) carbonate is typically accomplished through the reaction of 2-methoxyethanol with phosgene or safer phosgene substitutes such as triphosgene or diphenyl carbonate. This process mirrors the general methods used in the production of other dialkyl carbonates and has been well-documented in industrial and academic literature.

Bis(2-methoxyethyl) carbonate is primarily used as an intermediate in organic synthesis. Its carbonate group offers a reactive site for nucleophilic substitution, making it useful in the formation of polymers and in the synthesis of other organic compounds. It has applications in the development of specialty chemicals and has been explored as a reagent in certain transesterification reactions.

Additionally, bis(2-methoxyethyl) carbonate is employed as a solvent or solvent additive in some formulations. Its ether and carbonate functionalities contribute to a balance of polarity and volatility, which can be beneficial in specific industrial processes. However, its use as a solvent is less common compared to more established carbonates like dimethyl carbonate or diethyl carbonate.

The compound is also of interest in the context of green chemistry. Carbonates are generally considered more environmentally benign than halogenated solvents, and compounds like bis(2-methoxyethyl) carbonate have been evaluated for their potential role in sustainable synthesis and processing. Nevertheless, the presence of the methoxyethyl moiety requires attention due to the known toxicity associated with 2-methoxyethanol derivatives, necessitating appropriate safety measures during handling and use.

Overall, bis(2-methoxyethyl) carbonate is a functional and well-characterized chemical used in chemical synthesis and formulation work, valued for its reactivity and physical properties within specific industrial contexts.

References

2023. Molecularly engineered linear organic carbonates as practically viable nonflammable electrolytes for safe Li-ion batteries. Energy Environ. Sci., 16(7).
DOI: 10.1039/D3EE00157A

2023. Sustainable valorisation of renewables through dialkyl carbonates and isopropenyl esters. Green Chem., 25(13).
DOI: 10.1039/D2GC04145F

2021. High-voltage liquid electrolytes for Li batteries: progress and perspectives. Chem. Soc. Rev., 50(18).
DOI: 10.1039/D1CS00450F