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281662

Sigma-Aldrich

Diethylene glycol dimethyl ether

anhydrous, 99.5%

Synonym(s):

2-Methoxyethyl ether, Bis(2-methoxyethyl) ether, Dimethyldiglycol, ‘Diglyme’

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About This Item

Linear Formula:
(CH3OCH2CH2)2O
CAS Number:
Molecular Weight:
134.17
Beilstein:
1736101
EC Number:
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.21

grade

anhydrous

Quality Level

vapor density

4.6 (vs air)

vapor pressure

3 mmHg ( 20 °C)

Assay

99.5%

form

liquid

autoignition temp.

370 °F

expl. lim.

17.4 %

impurities

<0.005% water

evapn. residue

<0.0005%

refractive index

n20/D 1.408 (lit.)

pH

7 (20 °C)

bp

162 °C (lit.)

mp

−64 °C (lit.)

density

0.944 g/mL at 20 °C (lit.)
0.939 g/mL at 25 °C (lit.)

SMILES string

COCCOCCOC

InChI

1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3

InChI key

SBZXBUIDTXKZTM-UHFFFAOYSA-N

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General description

Diethylene glycol dimethyl ether is a hydrophilic electron-donor solvent.

Application

Diethylene glycol dimethyl ether may be used as a solvent in the following processes:
  • Synthesis of 3,5-dinitrobenzaldehyde via reduction of 3,5-dinitrobenzoyl chloride using lithium aluminum tri-tert-butoxyhydride.
  • Copper-catalyzed cross-coupling of iodoarenes with 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine to form the corresponding trifluoromethyl arenes.
  • Conversion of olefins (for eg: (±)-α-pinene) to primary amines (3-pinanamine) via hydroboration-amination reaction.

recommended

Pictograms

FlameHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 3 - Repr. 1B

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

134.6 °F - closed cup

Flash Point(C)

57 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Boranes in Functionalization of Olefins to Amines: 3-Pinanamine
Organic Syntheses, 58, 32-32 (1978)
Trifluoromethylation of Aryl Iodides Catalyzed by the
Copper(I)-Phen Complex
Shimizu N, et al
Organic Syntheses, 93, 147-162 (2016)
Catalytic activity of diethylene glycol dimethyl ethers in conversion of 6,7-dichloro-3-ethyl-2-ethoxynaphthazarine into echinochrome trimethyl ether.
Kochergina TY and Anufriev VF.
Russ. J. Org. Chem., 38(4), 534-537 (2002)
Kun Xue et al.
Biomaterials science, 8(3), 926-936 (2019-12-14)
Transparency is an important criterion for the application of biomaterials to the eye and essential for use as a vitreous substitute. However, there is a lack of understanding on the features of transparent hydrogels and the boundaries of transparency of
Simultaneous determination of six hydrophilic ethers at trace levels using coconut charcoal adsorbent and gas chromatography/mass spectrometry
Stepien DK and Puttmann W
Analytical and Bioanalytical Chemistry, 405(5), 1743-1751 (2013)

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