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674613 Aldrich

Tetrakis(dimethylamino)ethylene

Synonym: Octamethylethylenetetramine, TDAE

  • CAS Number 996-70-3

  • Linear Formula [(CH3)2N]2C=C[N(CH3)2]2

  • Molecular Weight 200.32

  •  Beilstein Registry Number 1705900

  •  EC Number 213-638-1

  •  MDL number MFCD00009601

  •  PubChem Substance ID 24885226

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Other Synthetic Reagents for C-C Bond Formation, Synthetic Reagents
InChI Key   CBXRMKZFYQISIV-UHFFFAOYSA-N
refractive index   n20/D 1.48(lit.)
bp   59 °C/0.9 mmHg(lit.)
density   0.861 g/mL at 25 °C(lit.)

Description

Application

Reagent used to convert α-bromoketones into 1,4-diketones.

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

Packaging

1, 10, 50 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2734PSN1 3(8) / PGII
WGK Germany 
3
Flash Point(F) 
127.4 °F
Flash Point(C) 
53 °C

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Protocols & Articles

Articles

Reagents for Fluorination

The trifluoromethyl substituent has long been recognized for the positive influence it can have on the biological activity of molecules. Professor William Dolbier, Jr. (University of Florida) has dev...
Aldrich ChemFiles 2007, 7.1, 11.

Tetrakis(dimethylamino)ethylene (TDAE)

In 2001, Professor William Dolbier, Jr., at the University of Florida reported1 an approach to nucleophilic trifluoromethylation based on the generation of a trifluoromethyl anion using CF3I in the p...
Mark Redlich
Aldrich ChemFiles 2008, 8.3, 8.
Keywords: Organic synthesis

Peer-Reviewed Papers
15

References

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