2-Methoxyethanol

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2-Methoxyethanol
2-Methoxyethanol
2-Methoxyethanol
Names
IUPAC name
2-Methoxyethanol
Other names
Ethylene glycol monomethyl ether
EGME
Methyl Cellosolve
Identifiers
109-86-4 YesY
ChEBI CHEBI:46790 YesY
ChEMBL ChEMBL444144 YesY
ChemSpider 7728 YesY
DrugBank DB02806 YesY
Jmol 3D model Interactive image
KEGG D05554 YesY
UNII EK1L6XWI56 YesY
Properties
C3H8O2
Molar mass 76.09 g/mol
Appearance Colorless liquid
Odor Ether-like[1]
Density 0.965 g/cm3
Melting point −85 °C (−121 °F; 188 K)
Boiling point 124 to 125 °C (255 to 257 °F; 397 to 398 K)
miscible[1]
Vapor pressure 6 mmHg (20°C)[1]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3
H
8
O
2
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated oxirane followed by proton transfer:

C
2
H
5
O+
+ CH
3
OH
C
3
H
8
O
2
+ 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 deicing solutions. In organometallic 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.

2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for granulocytopenia, macrocytic anemia, oligospermia, and azoospermia.[2]

The methoxyethanol is converted by alcohol dehydrogenase into methoxyacetic acid which is the substance which causes the harmful effects. Both ethanol and acetate have a protecting effect. The methoxyacetate can enter the Krebs cycle where it forms methoxycitrate.[3]

References

  1. 1.0 1.1 1.2 Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. Occupational exposure guidelines
  3. F. Welsch, Toxicology Letters, 2005, volume 156, pages 13-28