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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

Quality Level

100

Assay

97%

refractive index

n20/D 1.430

bp

189 °C/760 mmHg

density

0.841 g/mL at 25 °C

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.

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

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

Certificates of Analysis (COA)

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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)
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
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.

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