2-Methoxyethanol







































































































































2-Methoxyethanol

2-Methoxyethanol

2-Methoxyethanol
Names

IUPAC name
2-Methoxyethanol

Other names
Ethylene glycol monomethyl ether
EGME
Methyl Cellosolve

Identifiers

CAS Number

  • 109-86-4 ☑Y

3D model (JSmol)
  • Interactive image

ChEBI

  • CHEBI:46790 ☑Y

ChEMBL

  • ChEMBL444144 ☑Y

ChemSpider

  • 7728 ☑Y

DrugBank

  • DB02806 ☑Y

ECHA InfoCard
100.003.377

KEGG

  • D05554 ☑Y

UNII

  • EK1L6XWI56 ☑Y




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

NFPA 704


Flammability code 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 fuel
Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas
Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus
Special hazards (white): no codeNFPA 704 four-colored 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]
US health exposure limits (NIOSH):


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, 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 oxirane 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]



References




  1. ^ abcdefg "NIOSH Pocket Guide to Chemical Hazards #0401". National Institute for Occupational Safety and Health (NIOSH)..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ ab "Methyl cellosolve". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).


  3. ^ Occupational exposure guidelines


  4. ^ F. Welsch, Toxicology Letters, 2005, volume 156, pages 13-28









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