TETRAKIS(DIMETHYLAMINO)ETHYLENE Chemical Properties

Melting point:

>200 °C (decomp)

Boiling point:

98°C 25mm

Density 

0.861 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.48(lit.)

Flash point:

53°C

storage temp. 

0-10°C

pka

6.47±0.70(Predicted)

form 

clear liquid

color 

Light yellow to Yellow to Orange

BRN 

1705900

Stability:

Stable. Incompatible with acid chlorides, acids, strong oxidizing agents, acid anhydrides, carbon dioxide, oxygen, chlorinated solvents. Reacts with oxygen in air to give a greenish-yellow emission. Flammable.

CAS DataBase Reference

996-70-3

NIST Chemistry Reference

Tetrakis(dimethylamino)ethylene(996-70-3)

EPA Substance Registry System

Ethenetetramine, octamethyl- (996-70-3)

Safety Information

Hazard Codes 

C

Risk Statements 

10-34

Safety Statements 

16-27-36/37/39-45-26

RIDADR 

3286

WGK Germany 

3

HS Code 

2921.29.0055

HazardClass 

3.2

PackingGroup 

III

MSDS

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TETRAKIS(DIMETHYLAMINO)ETHYLENE Usage And Synthesis

Chemical Properties

light yellow-green liquid with an unpleasant

Uses

Involved in TDAE methodology for coupling and intramolecular Buchwald reactions

Acts as a reducing agent

Reactant involved in:

• Dioxygenation
• Insertion of aluminum anion into the C-N bond
• Chemiluminescent reactions with oxygen

reaction suitability

reaction type: C-C Bond Formation

Purification Methods

Impurities include tetramethylurea, dimethylamine, tetramethylethanediamine and tetramethyloxamide. It is washed with water while being flushed with nitrogen to remove dimethylamine, dried over molecular sieves, then passed through a silica gel column (previously activated at 400o) under nitrogen. De-gas it in a vacuum line by distillation from a trap at 50o to one at -70o. Finally, it is stirred over sodium-potassium alloy for several days. [Holroyd et al. J Phys Chem 89 4244 1985, Wiberg Angew Chem Int Ed Engl 7 766 1968, Beilstein 4 IV 167.]

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