TheInfoListRev V5.1.84
Xfr/

Topic summary

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 InfoCard100.005.455EC Number
  • 205-999-9
UNII
  • InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
    Key: IMNIMPAHZVJRPE-UHFFFAOYSA-N
  • 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 C6H12N2Molar mass112.176 g·mol Appearance White crystalline powder Melting point156 to 160 °C (313 to 320 °F; 429 to 433 K) Boiling point174 °C (345 °F; 447 K) Soluble, hygroscopic Acidity (pKa) 3.0, 8.8 (in water, for conjugated acid) Hazards Occupational safety and health (OHS/OSH):
Main hazards
Harmful GHS labelling: DangerH228, H302, H315, H319, H335, H412P210, P261, P273, P305+P351+P338NFPA 704 (fire diamond)
2
2
1
Flash point62 °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).
checkYverify (  ?)

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

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 adopt the boat conformations, not the usual chair conformations.

Wikipedia source