N,N,N',N'-Tetramethylethylenediamine Chemical Properties

Melting point:

−55 °C(lit.)

Boiling point:

120-122 °C(lit.)

Density 

0.775 g/mL at 20 °C(lit.)

vapor density 

4 (vs air)

vapor pressure 

21 hPa (20 °C)

refractive index 

n20/D 1.4179(lit.)

Flash point:

50 °F

storage temp. 

Store below +30°C.

solubility 

H₂O: 10 mg/mL at 20 °C, clear, colorless

form 

Liquid

pka

10.40, 8.26(at 25℃)

Specific Gravity

0.777 (20/4℃)

color 

Clear colorless to slightly yellow

Odor

Amine like

PH

8.0-8.5 (0.1g/l, H2O, 20℃)

explosive limit

1-9%(V)

Water Solubility 

miscible

Sensitive 

Hygroscopic

Merck 

14,9134

BRN 

1732991

Stability:

Stable. Highly flammable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, copper, mercury.

InChI

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

InChIKey

DMQSHEKGGUOYJS-UHFFFAOYSA-N

SMILES

CN(C)CCN(C)C

LogP

-0.13 at 20.2℃

CAS DataBase Reference

110-18-9(CAS DataBase Reference)

NIST Chemistry Reference

1,2-Ethanediamine, N,N,N',N'-tetramethyl-(110-18-9)

EPA Substance Registry System

Tetramethylethylenediamine (110-18-9)

Safety Information

Hazard Codes 

F,C,Xi

Risk Statements 

11-20/22-34-20/21/22

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 2372 3/PG 2

WGK Germany 

1

RTECS 

KV7175000

F 

3-8-10-34

Autoignition Temperature

145 °C

Hazard Note 

Irritant

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

II

HS Code 

29212900

Storage Class

3 - Flammable liquids

Hazard Classifications

Acute Tox. 3 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Flam. Liq. 2
Skin Corr. 1B

Hazardous Substances Data

110-18-9(Hazardous Substances Data)

MSDS

• Language:English Provider:TEMED
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N,N,N',N'-Tetramethylethylenediamine Usage And Synthesis

Chemical Properties

Colorless to slightly yellow liquid

Uses

N,N,N',N'-Tetramethylethylenediamine is used as polymerization accelerator in gel electrophoresis, solvent and oxidizing reagent. It is also used for the separation of proteins or nucleic acids. Further, it is employed as a ligand for metal ions like zinc and copper. It is actively involved in the formation of anionic organometallic complex.

Definition

ChEBI: N,N,N',N'-tetramethylethylenediamine is an ethylenediamine derivative in which each nitrogen carries two methyl substituents. It is widely employed both as a ligand for metal ions and as a catalyst in organic polymerisation. It has a role as a chelator and a catalyst.

Application

N,N,N',N'-Tetramethylethylenediamine (TMEDA) is a highly efficient catalyst for the Baylis-Hillman reaction, outperforming the most widely used catalyst DABCO. TMEDA can catalyze the Baylis-Hillman reaction of aromatic aldehydes with various active olefins.^[1]

General Description

1,2-di-(dimethylamino)ethane appears as a water-white colored liquid with a fishlike odor. Flash point 68 °F. Less dense than water. Vapors heavier than air. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Slightly soluble in water. Sensitive to heat and may be sensitive to air .

Reactivity Profile

N,N,N',N'-Tetramethylethylenediamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by ingestion. Mddly toxic by slun contact. A skin and severe eye irritant. Flammable when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits toxic fumes of NOx. See also MINES.

Synthesis

A method for preparing a catalyst for the direct amination of dimethylethanolamine to produce N,N,N',N'-tetramethylethylenediamine: comprising the following steps: (1) Weighing approximately 24.2 g of Cu(NO?)???3H?O, 14.5 g Ni(NO?)???6H?O and 37.5 g Al(NO?)???9H?O, dissolving in 100 mL deionised water; (2) Weigh 18.0 g of NaOH sufficient to completely precipitate the metal ions as the precipitating agent, dissolving it in deionised water to prepare a 2 mol/L solution; (3) Under stirring and at a water bath temperature of 80??C, slowly add the nitrate solution prepared in step (1) to the NaOH solution prepared in step (2) dropwise until the pH reaches 8.0; (4) Stir for 4 hours at this temperature, then allow to stand and age for 12 hours at the same temperature. (5) Vacuum-filter the aged catalyst, wash repeatedly with deionised water until filtrate pH reaches 7.0; dry the filter cake for 32 hours; grind the dried catalyst into powder, then calcine at 450??C for 4 hours to obtain the catalyst precursor; (6) The calcined catalyst was compressed into tablets, cut and sieved to obtain 20?C40 mesh finished catalyst Ni-Cu/Al?O? (20 mL). Under specified temperature, pressure, space velocity and molar ratio conditions, dimethylethanolamine, dimethylamine and hydrogen were continuously fed. Following gas-liquid separation of the product, the liquid phase was analysed. The conversion rate of dimethylethanolamine reached 87.6%, with an N,N,N',N'-tetramethylethylenediamine selectivity of 78.3%.

Purification Methods

Dry TMEDA partially with molecular sieves (Linde type 4A), then distil it in a vacuum from butyl lithium. This treatment removes all traces of primary and secondary amines and water. [Hay et al. J Chem Soc, Faraday Trans 1 68 1 1972.] Or dry it with KOH pellets, reflux for 2hours with one-sixth its weight of n-butyric anhydride (to remove primary and secondary amines) and fractionally distil it. Reflux it with fresh KOH, and distil it under nitrogen. [Cram & Wilson J Am Chem Soc 85 1245 1963.] It was also distilled from Na. Store it sealed under N2. The dipicrate has m 263o(dec). [Beilstein 4 H 250, 4 I 415, 4 II 690, 4 III 512, 4 IV 1172.]

References

[1] SANHU ZHAO  Zhao bin C. The N,N,N′,N′–Tetramethylethylenediamine Mediated Baylis‐Hillman Reaction[J]. Synthetic Communications, 2005, 35 1: 121-127. DOI:10.1081/SCC-200046521.

N,N,N',N'-Tetramethylethylenediamine(110-18-9)Related Product Information

• N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine
• 3-Dimethylaminopropylamine
• Triacetonediamine
• N,N-Dimethylethylenediamine
• ETHANE
• N-(1-Naphthyl)ethylenediamine dihydrochloride
• 2-(2-Aminoethylamino)ethanol
• Pinacol
• 2-Aminoethyl(ethyl)amine
• N-METHYLETHYLENEDIAMINE
• Hexafluoroethane
• Tetramethylammonium bromide
• Tetrabutylammonium hydrogen sulfate
• Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate
• Tetrabutylammonium bromide
• 2,2,6,6-Tetramethyl-4-piperidinol
• N,N,N',N'-Tetramethyl-1,6-hexanediamine
• Actinomycin D