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2-Methoxyethanol

2-Methoxyethanol
2-Methoxyethanol
2-Methoxyethanol
Names
Preferred IUPAC name
2-Methoxyethan-1-ol
Other names
Ethylene glycol monomethyl ether
EGME
Methyl Cellosolve
2-MOE
Identifiers
3D model (JSmol)
1731074
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.377
EC Number
  • 203-713-7
81877
KEGG
RTECS number
  • KL5775000
UNII
UN number 1188
  • InChI=1S/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3 checkY
    Key: XNWFRZJHXBZDAG-UHFFFAOYSA-N checkY
  • InChI=1/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3
    Key: XNWFRZJHXBZDAG-UHFFFAOYAC
  • OCCOC
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]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H302, H312, H332, H360
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
2
2
Flash point 39 °C (102 °F; 312 K)
Explosive limits 1.8%-14%[1]
Lethal dose or concentration (LD, LC):
2370 mg/kg (rat, oral)
890 mg/kg (rabbit, oral)
1480 mg/kg (mouse, oral)
950 mg/kg (guinea pig, oral)[2]
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]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 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]

Presence in interstellar space

In 2024, a group led by researchers at the Massachusetts Institute of Technology reported the discovery of 2-methoxyethanol in a star-forming region within the nebula NGC 6334.[5] The discovery was made by examining in the laboratory the spectral signature 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, and 25 of its spectral lines were detected, constituting a secure identification of the molecule in the astronomical data.

References

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0401". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Methyl cellosolve". Immediately Dangerous to Life or 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
  5. ^ Fried, Z.T.P.; et al. (20 April 2024). "Rotational Spectrum and First Interstellar Detection of 2-methoxyethanol Using ALMA Observations of NGC 6334I". The Astrophysical Journal Letters. 965 (2): L23. arXiv:2403.17341. Bibcode:2024ApJ...965L..23F. doi:10.3847/2041-8213/ad37ff. ISSN 2041-8213.
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