Dimethoxyethane

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether[2]. It is commonly used as a solvent in batteries and in organometallic reaction chemistry due to its higher boiling point compared to diethyl ether and THF[1][2]. Additionally, it is miscible with water[1][2].

Molecular Formula and CAS Number

The molecular formula for dimethoxyethane is C4H10O2, and its CAS number is 110-71-4[1][2].

Physical Properties

Dimethoxyethane is a clear, colorless liquid with a boiling point of 396°F (202°C)[4]. It has a density of 0.867 g/mL at 25°C and a refractive index of 1.379[4]. The vapor pressure at 20°C is 48 mmHg[4].

Production

Dimethoxyethane is produced industrially by the reaction of dimethylether with ethylene oxide[2].

Applications

Dimethoxyethane is used as a solvent in lithium batteries, particularly in combination with a high-permittivity solvent like propylene carbonate[2]. It is also used as a coordinating solvent in the laboratory and acts as a bidentate ligand for some metal cations[2]. It is often used in organometallic chemistry for reactions such as Grignard reactions and hydride reductions[2]. Furthermore, it is suitable for palladium-catalyzed reactions including Suzuki reactions and Stille couplings[2].

Safety and Handling

Dimethoxyethane is considered hazardous and is classified as a highly flammable liquid and vapor, causing skin irritation and serious eye irritation[3]. It is also harmful if inhaled and may damage fertility or the unborn child[3]. Handling precautions include obtaining special instructions before use and not handling until all safety precautions have been read and understood[3].

Availability and Pricing

Dimethoxyethane is available from various suppliers, including Spectrum Chemical, where it can be purchased for as low as $113.30[1]. It is also available from Sigma-Aldrich in different grades, including ReagentPlus and anhydrous forms[4][5].

Citations:

[1] https://www.spectrumchemical.com/12-dimethoxyethane-d1350

[2] https://en.wikipedia.org/wiki/Dimethoxyethane

[3] https://www.fishersci.com/store/msds?countryCode=US&language=en&partNumber=O24304&productDescription=1%2C2-DIMETHOXYETHANE+CERT+4L&vendorId=VN00033897

[4] https://www.sigmaaldrich.com/US/en/product/sigald/e27408

[5] https://www.sigmaaldrich.com/US/en/product/sial/259527