2-Methoxyethanol

2-Methoxyethanol
Names
	Preferred IUPAC name 2-Methoxyethan-1-ol
	Other names Ethylene glycol monomethyl ether; EGME; Methyl Cellosolve; 2-MOE
Identifiers
CAS Number	109-86-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1731074
ChEBI	CHEBI:46790 ;
ChEMBL	ChEMBL444144 ;
ChemSpider	7728 ;
DrugBank	DB02806 ;
ECHA InfoCard	100.003.377
EC Number	203-713-7;
Gmelin Reference	81877
KEGG	D05554 ;
PubChem CID	8019;
RTECS number	KL5775000;
UNII	EK1L6XWI56 ;
UN number	1188
CompTox Dashboard (EPA)	DTXSID101349127, DTXSID10872619 DTXSID5024182, DTXSID101349127, DTXSID10872619 ;
	InChI InChI=1S/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3 Key: XNWFRZJHXBZDAG-UHFFFAOYSA-N ; InChI=1/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3 Key: XNWFRZJHXBZDAG-UHFFFAOYAC;
	SMILES OCCOC;
Properties
Chemical formula	C3H8O2
Molar mass	76.09 g/mol
Appearance	Colorless liquid
Odor	Ether-like
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
Vapor pressure	6 mmHg (20°C)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H332, H360
Precautionary statements	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)	3 2 2
Flash point	39 °C (102 °F; 312 K)
Explosive limits	1.8%-14%
	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)
LC50 (median concentration)	1480 ppm (mouse, 7 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (80 mg/m3) [skin]
REL (Recommended)	TWA 0.1 ppm (0.3 mg/m3) [skin]
IDLH (Immediate danger)	200 ppm
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). verify (what is ?) Infobox references

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

^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0401". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Methyl cellosolve". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "Occupational exposure guidelines". Archived from the original on 2016-08-22. Retrieved 2014-03-28.
^ F. Welsch, Toxicology Letters, 2005, volume 156, pages 13-28
^ 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.

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0401". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-2] "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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