MilliporeSigma
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411019

Sigma-Aldrich

N,N,N′,N′-Tetramethylethylenediamine

≥99.5%, purified by redistillation

Synonym(s):
TEMED, 1,2-Bis(dimethylamino)ethane, TMEDA
Linear Formula:
(CH3)2NCH2CH2N(CH3)2
CAS Number:
Molecular Weight:
116.20
Beilstein:
1732991
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99.5%

form

liquid

purified by

redistillation

expl. lim.

9.08 %

refractive index

n20/D 1.4179 (lit.)

bp

120-122 °C (lit.)

mp

−55 °C (lit.)

density

0.775 g/mL at 20 °C (lit.)

SMILES string

CN(C)CCN(C)C

InChI

1S/C6H16N2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3

InChI key

KWYHDKDOAIKMQN-UHFFFAOYSA-N

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General description

N,N,N′,N′-Tetramethylethylenediamine (TMEDA) is a bidentate tertiary amine. It is a Lewis base having good solvating properties. It is useful ligand for organolithium chemistry. Ultrafast molecular structural dynamics of the charge transfer in N,N,N′,N′-tetramethylethylenediamine has been studied by Rydberg fingerprint spectroscopy.

Packaging

1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

61.7 °F - closed cup

Flash Point(C)

16.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Is N, N, N', N'-tetramethylethylenediamine a good ligand for lithium?
Collum DB.
Accounts of Chemical Research, 25(10), 448-454 (1992)
Xinxin Cheng et al.
The journal of physical chemistry. A, 119(12), 2813-2818 (2015-02-26)
We have explored the ultrafast molecular structural dynamics associated with charge transfer in N,N,N',N'-tetramethylethylenediamine using Rydberg fingerprint spectroscopy in conjunction with self-interaction corrected density functional theory. Excitation at 239 nm prepares the molecule in the Franck-Condon region of the 3s
Hajime Mori et al.
The Journal of organic chemistry, 71(24), 9004-9012 (2006-11-18)
The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D(2)O quenching. In this paper, the full details of the examples of
Marina V Novoselova et al.
Colloids and surfaces. B, Biointerfaces, 181, 680-687 (2019-06-22)
High intensity focused ultrasound (HIFU) is widely used in medical practice, including cancer therapy. Also this approach is promising for remote release of encapsulated drugs in various other biomedical applications where local treatment is needed. Our approach underpins the minimization
Organometallic p-complexes XII. The metalation of benzene and ferrocene by n-butyllithium-N, N, N', N'-tetramethylethylenediamine
Rausch MD and Ciappenelli DJ.
Journal of Organometallic Chemistry, 10(1), 127-136 (1967)

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