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Merck

E27408

1,2-Dimethoxyethane

ReagentPlus®, ≥99%, inhibitor-free

Synonym(s):

mono-Glyme, Dimethylglycol, Ethylene glycol dimethyl ether, Monoglyme

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About This Item

Linear Formula:
CH3OCH2CH2OCH3
CAS Number:
110-71-4
Molecular Weight:
90.12
UNSPSC Code:
12352112
NACRES:
NA.21
PubChem Substance ID:
329799037
EC Number:
203-794-9
Beilstein/REAXYS Number:
1209237
MDL number:
MFCD00008502
Assay:
≥99%
Bp:
85 °C (lit.)
Vapor pressure:
48 mmHg ( 20 °C)

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InChI key

XTHFKEDIFFGKHM-UHFFFAOYSA-N

InChI

1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3

SMILES string

COCCOC

vapor density

3.1 (20 °C, vs air)

vapor pressure

48 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

form

liquid

autoignition temp.

396 °F

expl. lim.

10.4 %

dilution

(for general lab use)

impurities

≤0.5% (water)

refractive index

n20/D 1.379 (lit.)

pH

7

bp

85 °C (lit.)

mp

−58 °C (lit.)

density

0.867 g/mL at 25 °C (lit.)

Quality Level

100

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General description

1,2-Dimethoxyethane (DME) is an inert aprotic polar solvent for electrolytes of lithium batteries, polysilicones, oligo- and polysaccharides.

Application

1,2-Dimethoxyethane can be used as a solvent to synthesize:
  • Oxazoles from α-acylamino ketones via Robinson-Gabriel reaction.
  • 5-Arylhistidines via Suzuki-Miyaura cross-coupling between 5-bromohistidine and arylboronic acids.
  • Aryl thioethers via Pd-catalyzed thioetherification of aryl halides with aliphatic and aromatic thiols.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Flam. Liq. 2 - Repr. 1B - Skin Irrit. 2

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

41.0 °F - closed cup

flash_point_c

5 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6406
SHBT0952
SHBS8757
SHBR1819
STBK8943

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Tetrahedron Letters, 34, 4591-4591 (1993)
Organometallics, 13, 1498-1498 (1994)
Inorganic Chemistry, 33, 1685-1685 (1994)
Andrew Martins et al.
Organic letters, 12(22), 5186-5188 (2010-10-19)
A palladium-catalyzed crossed biaryl coupling/reduction sequence enables the formation of meta-substituted biaryls via solvent-mediated arylpalladium(II) reduction. Isotope labeling studies determined that the decomposition of 1,2-dimethoxyethane (DME) is indeed involved in the reductive process.
Peter A Campochiaro et al.
Ophthalmology, 122(3), 545-554 (2014-12-03)
AKB-9778 is a small-molecule competitive inhibitor of vascular endothelial-protein tyrosine phosphatase (VE-PTP) that promotes Tie2 activation and reduces vascular leakage and neovascularization in mouse models. The purpose of this study was to test the safety, tolerability, pharmacokinetics, and biological activity
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