DABCO
Chemical compound / From Wikipedia, the free encyclopedia
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]
Quick Facts Names, Identifiers ...
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Names | |||
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Preferred IUPAC name
1,4-Diazabicyclo[2.2.2]octane | |||
Other names
Triethylenediamine, TEDA | |||
Identifiers | |||
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3D model (JSmol) |
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ChEBI | |||
ChEMBL | |||
ChemSpider |
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ECHA InfoCard | 100.005.455 | ||
EC Number |
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PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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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: | |||
Danger | |||
H228, H302, H315, H319, H335, H412 | |||
P210, P261, P273, P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
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).
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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.