2-Methoxyethanol, or methyl cellosolve, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with formula that is used mainly as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

. It is a clear, colorless liquid with an

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

-like odor. It is in a class of solvents known as

glycol ethers Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while h ...

which are notable for their ability to dissolve a variety of different types of chemical compounds and for their

miscibility Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). Such substances are said to be miscible (etymologically ...

with water and other solvents. It can be formed by the nucleophilic attack of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

on protonated

ethylene oxide Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless ...

followed by proton transfer: : + → + 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 deicing solutions. In

organometallic Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

chemistry it is commonly used for the synthesis of Vaska's complex and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and

carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

. 2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for

granulocytopenia Granulocytes are cells in the innate immune system characterized by the presence of specific granules in their cytoplasm. Such granules distinguish them from the various agranulocytes. All myeloblastic granulocytes are polymorphonuclear, that is ...

, macrocytic anemia, oligospermia, and azoospermia. The methoxyethanol is converted by

alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...

into methoxyacetic acid which is the substance which causes the harmful effects. Both

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

and

acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...

have a protecting effect. The methoxyacetate can enter the

Krebs cycle The citric acid cycle—also known as the Krebs cycle, Szent–Györgyi–Krebs cycle, or TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions that release the energy stored in nutrients through acetyl-CoA oxidation. The e ...

where it forms methoxy

citrate Citric acid is an organic compound with the formula . It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry Biochemistry, or biological chemistry, is the study of chemical processes within and relati ...

Presence in interstellar space

In 2024, a group led by researchers at the

Massachusetts Institute of Technology The Massachusetts Institute of Technology (MIT) is a Private university, private research university in Cambridge, Massachusetts, United States. Established in 1861, MIT has played a significant role in the development of many areas of moder ...

reported the discovery of 2-methoxyethanol in a star-forming region within the nebula NGC 6334. The discovery was made by examining in the laboratory the

spectral signature Spectral signature is the variation of reflectance or emittance of a material with respect to wavelengths (i.e., reflectance/emittance as a function of wavelength). The spectral signature of stars indicates the composition of the stellar atmosph ...

of 2-methoxyethanol as the molecule was made to rotate. This signature was then sought in observational data for the region collected by the

Atacama Large Millimeter Array The Atacama Large Millimeter/submillimeter Array (ALMA) is an astronomical interferometer of 66 radio telescopes in the Atacama Desert of northern Chile, which observe electromagnetic radiation at millimeter and submillimeter wavelengths. The ar ...

, and 25 of its spectral lines were detected, constituting a secure identification of the molecule in the astronomical data.

References

{{DEFAULTSORT:Methoxyethanol, 2- Glycol ethers Hydroxyethyl compounds