2-Methoxyethanol

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
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 ethylene oxide followed by proton transfer:

C
2H
5O+
 + CH
3OH → C
3H
8O
2 + H+
2-Methoxyethanol
Names
IUPAC name
2-Methoxyethanol
Other names
Ethylene glycol monomethyl ether
EGME
Methyl Cellosolve
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1731074
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.377
EC Number
  • 203-713-7
Gmelin Reference
 81877
KEGG
PubChem CID
RTECS number
  • KL5775000
UNII
UN number 1188
CompTox Dashboard (EPA)
Properties
Chemical formula
 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)
Solubility in water
 miscible[1]
Vapor pressure 6 mmHg (20°C)[1]
Hazards
Safety data sheet External MSDS
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H302, H312, H332, H360
GHS precautionary statements
 P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P303+361+353, P304+312, P304+340, P308+313, P312, P322, P330, P363, P370+378
NFPA 704 (fire diamond)
2
3
2
Flash point 39 °C (102 °F; 312 K)
Explosive limits 1.8%-14%[1]
Lethal dose or concentration (LD, LC):
LDLo (lowest published)
 2370 mg/kg (rat, oral)
890 mg/kg (rabbit, oral)
1480 mg/kg (mouse, oral)
950 mg/kg (guinea pig, oral)[2]
LC50 (median concentration)
 1480 ppm (mouse, 7 hr)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (80 mg/m3) [skin][1]
REL (Recommended)
 TWA 0.1 ppm (0.3 mg/m3) [skin][1]
IDLH (Immediate danger)
 200 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[3]

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.[4]

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0401". National Institute for Occupational Safety and Health (NIOSH).
  2. "Methyl cellosolve". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. "Occupational exposure guidelines". Archived from the original on 2016-08-22. Retrieved 2014-03-28.
  4. F. Welsch, Toxicology Letters, 2005, volume 156, pages 13-28
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