2-Methoxyethanol

2-Methoxyethanol, or methyl cellosolve, is an <a href="/facts/Organic_compound/gqCNaN45">organic compound</a> with formula C3H8O2 that is used mainly as a <a href="/facts/Solvent/LoMPMz8S">solvent</a>. It is a clear, colorless liquid with an <a href="/facts/Diethyl_ether/Ep20vEdj">ether</a>-like odor. It is in a class of solvents known as <a href="/facts/Glycol_ethers/4LL9PrnU">glycol ethers</a> which are notable for their ability to dissolve a variety of different types of chemical compounds and for their <a href="/facts/Miscibility/HwQaolbQ">miscibility</a> with water and other solvents. It can be formed by the <a href="/facts/Nucleophile/xYccoaJQ">nucleophilic</a> attack of <a href="/facts/Methanol/EIfpoNCg">methanol</a> on <a href="/facts/Protonation/q5Gf9z0M">protonated</a> <a href="/facts/Ethylene_oxide/4WDVKX2r">ethylene oxide</a> followed by proton transfer:

C2H5O+ + CH3OH → C3H8O2 + H+
2-Methoxyethanol is used as a solvent for many different purposes such as varnishes, dyes, and resins. It is also used as an additive in airplane <a href="/facts/Deicing_fluid/hNyJUukW">deicing solutions</a>. In <a href="/facts/Organometallic/bhqFz2P0">organometallic</a> chemistry it is commonly used for the synthesis of <a href="/facts/Vaska%27s_complex/uT2meu8D">Vaska's complex</a> and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and <a href="/facts/Carbon_monoxide/CKuLtEMJ">carbon monoxide</a>.
2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for <a href="/facts/Granulocytopenia/zsE3ldLb">granulocytopenia</a>, <a href="/facts/Macrocytic_anemia/EyUTHKno">macrocytic anemia</a>, <a href="/facts/Oligospermia/BqvWzAVN">oligospermia</a>, and <a href="/facts/Azoospermia/5kycIv0S">azoospermia</a>.
The methoxyethanol is converted by <a href="/facts/Alcohol_dehydrogenase/XWwHgyad">alcohol dehydrogenase</a> into <a href="/facts/Methoxyacetic_acid/DaJdUorP">methoxyacetic acid</a> which is the substance which causes the harmful effects. Both <a href="/facts/Ethanol/3lCLfBSP">ethanol</a> and <a href="/facts/Acetate/U90VVczy">acetate</a> have a protecting effect. The methoxyacetate can enter the <a href="/facts/Krebs_cycle/EGJL9NXP">Krebs cycle</a> where it forms methoxy<a href="/facts/Citrate/EgKGQBdl">citrate</a>.

2-Methoxyethanol open-in-new

2-Methoxyethanol