Tetramethylethylenediamine

Structural formula
General
Surname	Tetramethylethylenediamine
other names	N , N , N ', N ' -tetramethylethane-1,2-diamine TMEDA TEMED
Molecular formula	C 6 H 16 N 2
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
CAS number 110-18-9 EC number 203-744-6 ECHA InfoCard 100.003.405 PubChem 123390 Wikidata Q417713
properties
Molar mass	116.2 g mol −1
Physical state	liquid
density	0.77 g cm −3
Melting point	−55 ° C
boiling point	120 ° C
solubility	soluble in water
Refractive index	1.4179 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-332-302-314 P: 210-280-305 + 351 + 338-310
Toxicological data	268 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N , N , N ′, N ′ -Tetramethylethylenediamine (TMEDA) is a chemical compound from the group of aliphatic amines .

properties

N , N , N ', N ' -Tetramethylethylenediamine is a highly flammable, clear, colorless liquid with an amine-like odor, which is easily soluble in water. It decomposes when heated, producing nitrogen oxides , carbon monoxide and carbon dioxide .

use

Tetramethylethylenediamine is a polymerization catalyst . It is therefore used, for example, together with ammonium persulfate for the polymerization of acrylamide in the production of polyacrylamide gels .

TMEDA is also used as a deaggregation additive in lithiation reactions. The addition of TMEDA enables high conversions in the ortholithiation of benzyl alcohol with n -BuLi in n -hexane.

safety instructions

The vapors of N , N , N ', N ' -Tetramethylethylenediamine can form an explosive mixture with air ( flash point 19 ° C, ignition temperature 145 ° C).

See also

• Ethylenediamine

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on N, N, N ′, N′-tetramethylethylenediamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-480.
3. ↑ Entry on N, N, N ′, N′-tetramethylethylenediamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Norbert Meyer, Dieter Seebach: Direct ortho-metalation of benzyl alcohols: A novel production of ortho-substituted benzyl alcohols. In: Chemical Reports. 113, 1980, pp. 1304-1319, doi : 10.1002 / cber.19801130410 .