DABCO

DABCO
Names
Preferred IUPAC name
1,4-Diazabicyclo[2.2.2]octane
Other names
Triethylenediamine, TEDA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.455 Edit this at Wikidata
EC Number
  • 205-999-9
UNII
  • InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2 checkY
    Key: IMNIMPAHZVJRPE-UHFFFAOYSA-N checkY
  • InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
    Key: IMNIMPAHZVJRPE-UHFFFAOYSA-N
  • InChI=1/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
    Key: IMNIMPAHZVJRPE-UHFFFAOYAP
  • C1CN2CCN1CC2
  • N12CCN(CC1)CC2
Properties
C6H12N2
Molar mass 112.176 g·mol−1
Appearance White crystalline powder
Melting point 156 to 160 °C (313 to 320 °F; 429 to 433 K)
Boiling point 174 °C (345 °F; 447 K)
Soluble, hygroscopic
Acidity (pKa) 3.0, 8.8 (in water, for conjugated acid)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H228, H302, H315, H319, H335, H412
P210, P261, P273, P305+P351+P338
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
2
1
Flash point 62 °C (144 °F; 335 K)
Related compounds
Related compounds
 Quinuclidine
Tropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

DABCO (1,4-diazabicyclo[2.2.2]octane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.[3]

It is similar in structure to quinuclidine, but the latter has one of the nitrogen atoms replaced by a carbon atom. Regarding their structures, both DABCO and quinuclidine are unusual in that the methylene hydrogen atoms are eclipsed within each of the three ethylene linkages. Furthermore, the diazacyclohexane rings, of which there are three, adopt the boat conformations, not the usual chair conformations.

  1. ^ D. H. Ripin; D. A. Evans (2002). "pKa's of Nitrogen Acids" (PDF).
  2. ^ "Safety data for 1,4-diazabicyclo[2.2.2]octane (see MSDS)". Sigma-Aldrich.
  3. ^ Uppuluri V. Mallavadhani, Nicolas Fleury-Bregeot. "1,4-Diazabicyclo [2.2.2]octane". In Encyclopedia of Reagents for Organic Synthesis, 2010, John Wiley & Sons, Ltd. doi:10.1002/047084289X.rd010m.pub2