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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:
111-96-6
Molecular Weight:
134.17
Beilstein:
1736101
EC Number:
203-924-4
MDL number:
MFCD00008503
UNSPSC Code:
12352112
PubChem Substance ID:
57648291
NACRES:
NA.21

grade

anhydrous

Quality Level

100

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

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Description
Pricing

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H226,H360FD

Hazard Classifications

Flam. Liq. 3 - Repr. 1B

Supplementary Hazards

EUH019

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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)
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)
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)
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