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Sigma-Aldrich

Bis[2-(N,N-dimethylamino)ethyl] ether

97%

Synonym(s):

2,2′-Oxybis(N,N-dimethylethylamine), 2-(Dimethylamino)ethyl ether

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About This Item

Linear Formula:
((CH3)2N(CH2CH2))2O
CAS Number:
3033-62-3
Molecular Weight:
160.26
EC Number:
221-220-5
MDL number:
MFCD00059199
UNSPSC Code:
12352100
PubChem Substance ID:
24884926
NACRES:
NA.22
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Assay

97%

refractive index

n20/D 1.430

bp

189 °C/760 mmHg

density

0.841 g/mL at 25 °C

functional group

amine
ether

SMILES string

CN(C)CCOCCN(C)C

InChI

1S/C8H20N2O/c1-9(2)5-7-11-8-6-10(3)4/h5-8H2,1-4H3

InChI key

GTEXIOINCJRBIO-UHFFFAOYSA-N

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General description

2-(Dimethylamino)ethyl ether is a tridentate ligand. It assists in the formation and stabilization of intermediates during the exchange reactions.[1]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H302 + H332,H311,H314

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

151.0 °F

Flash Point(C)

66.11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK0988
MKCK0987
SHBK8568
SHBK2521
SHBJ9419

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B Ballantyne
Veterinary and human toxicology, 39(5), 290-295 (1997-10-06)
Bis[2-(dimethylamino)ethyl]ether (DMAEE; CAS No 3033-62-3) is an industrial liquid chemical used principally as an amine catalyst. It was investigated for potential acute hazards. DMAEE is of moderate acute peroral toxicity with LD50 values in the rat of 1045 ml/kg and
Bis[2-(dimethylamino)ethyl]ether(CH3)2NCH2CH2OCH2CH2N(CH3)2.
B Ballantyne
Journal of applied toxicology : JAT, 25(3), 260-269 (2005-04-28)
Chao-Shan Da et al.
Organic letters, 11(24), 5578-5581 (2009-11-17)
Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O(i-)Pr)(4)
Mild Iodine- Magnesium Exchange of Iodoaromatics Bearing a Pyrimidine Ring with Isopropylmagnesium Chloride
Wang XJ, et al.
Organic Letters, 8, 3141-3144 (2006)
Se-Ra Shin et al.
Molecules (Basel, Switzerland), 24(7) (2019-04-10)
Isosorbide (ISB), a nontoxic bio-based bicyclic diol composed from two fuzed furans, was incorporated into the preparation of flexible polyurethane foams (FPUFs) for use as a cell opener and to impart antioxidant properties to the resulting foam. A novel method

Articles

Mild Mg – Halogen Exchange

Substantial progress has been made in magnesium–halogen exchange reactions used for the preparation of functionalized Grignard reagents containing sensitive moieties such as ester or cyano groups.

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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