Triazabicyclodecene

Source: Wikipedia, the free encyclopedia.
Triazabicyclodecene[1]
Names
Preferred IUPAC name
1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine
Other names
1,5,7-Triazabicyclo[4.4.0]dec-5-ene
TBD
Hexahydropyrimidopyrimidine
hpp
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.024.880 Edit this at Wikidata
EC Number
  • 227-367-1
UNII
  • InChI=1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9) checkY
    Key: FVKFHMNJTHKMRX-UHFFFAOYSA-N checkY
  • InChI=1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
    Key: FVKFHMNJTHKMRX-UHFFFAOYAP
  • N\2=C1/NCCCN1CCC/2
Properties
C7H13N3
Molar mass 139.20 g/mol
Melting point 125 to 130 °C (257 to 266 °F; 398 to 403 K)
Acidity (pKa) 15.2 ± 1.0[2] (pKa of conjugate acid in water); 26.03[3] (pKa of conjugate acid in acetonitrile)
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Triazabicyclodecene (1,5,7-triazabicyclo[4.4.0]dec-5-ene or TBD) is an

bicyclic guanidine. For a charge-neutral compound, it is a relatively strong base that is effective for a variety of organic transformations. TBD is colorless solid that is soluble in a variety of solvents.[4]

Reactivity

Mechanism proposed for the ring-opening polymerization of caprolactone to polycaprolactone by TBD.[5][6]

As a strong base, TBD fully

nitroaldol reactions), transesterification reactions, and Knoevenagel condensations.[8]

Deprotonation at the 7-position gives a particularly electron-rich ligand as manifested in the redox properties of ditungsten tetra(hpp).

See also

References

  1. ^ 1,5,7-Triazabicyclo[4.4.0]dec-5-ene at Sigma-Aldrich
  2. doi:10.5562/cca2472
    .
  3. PMID 15675863
    .
  4. ISBN 978-0-471-93623-7
    .
  5. PMID 16594676
    .
  6. polydispersity index
    1.16
  7. doi:10.1016/j.molstruc.2007.01.005
    .
  8. doi:10.1016/j.tetlet.2007.03.146
    .
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