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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
Assay:
99.5%
bp:
162 °C (lit.)
vapor pressure:
3 mmHg ( 20 °C)
Pricing and availability is not currently available.

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[1] electron-donor solvent.[2]

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.[3]
  • Copper-catalyzed cross-coupling of iodoarenes with 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine to form the corresponding trifluoromethyl arenes.[4]
  • Conversion of olefins (for eg: (±)-α-pinene) to primary amines (3-pinanamine) via hydroboration-amination reaction.[5]

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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Certificates of Analysis (COA)

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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)
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)
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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