2-Methoxyethanol
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula 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 ethylene oxide 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 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.

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.
Q174211
organic compound
Concept
Q146505
solvent
Concept
Q202218
ether
Concept
Q53844
glycol ethers
Concept
Q745930
nucleophilic
UNK
Q14982
methanol
Concept
Q899488
protonated
Concept
Q407473
ethylene oxide
Concept
Q4381762
deicing solutions
Concept
Q237200
organometallic
Concept
Q421607
Vaska's complex
Concept
Q2025
carbon monoxide
Concept
Q223143
granulocytopenia
Concept
Q2070695
macrocytic anemia
Concept
Q1876491
oligospermia
UNK
Q794026
azoospermia
Concept
Q410754
alcohol dehydrogenase
Concept
None
methoxyacetic acid
UNK
Q153
ethanol
Concept
Q212527
acetate
Concept
Q133895
Krebs cycle
Concept
Q159683
citrate
Concept
Q903362
2-Methoxyethanol
Concept
Q903362
2-Methoxyethanol
Concept
Q903362
2-Methoxyethanol
Concept
+2^^http://www.w3.org/2001/XMLSchema#decimal
2
NUMBER
+2^^http://www.w3.org/2001/XMLSchema#decimal
2
NUMBER
+2^^http://www.w3.org/2001/XMLSchema#decimal
2
NUMBER
instance of