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Triazabicyclodecene

Chemical compound From Wikipedia, the free encyclopedia

Triazabicyclodecene (1,5,7-triazabicyclo[4.4.0]dec-5-ene or TBD) is an organic compound consisting of a 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]

Quick facts Names, Identifiers ...
Triazabicyclodecene
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
  • Hexahydropyrimidopyrimidine
Identifiers
3D model (JSmol)
Abbreviations
  • TBD
  • Hhpp
ChEBI
ChemSpider
ECHA InfoCard 100.024.880 Edit this at Wikidata
EC Number
  • 227-367-1
UNII
UN number 1759
  • 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[1]
C7H13N3
Molar mass 139.20 g/mol
Appearance Light yellow crystals
Melting point 125 to 130 °C (257 to 266 °F; 398 to 403 K)
Soluble
Solubility in dimethylformamide 30 mg/ml[2]
Solubility in dimethyl sulfoxide 30 mg/ml[2]
Solubility in ethanol 30 mg/ml[2]
Solubility in Phosphate-buffered saline 2 mg/ml (pH 7.2)[2]
Acidity (pKa) 15.2±1.0[3]
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H412
P260, P264, P270, P273, P280, P301+P312+P330, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P405, P501
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactivity

Mechanism proposed for the ring-opening polymerization of caprolactone to polycaprolactone by TBD.[5][note 1]

As a strong base, TBD fully deprotonates most phenols, carboxylic acids, and some carbon acids.[6]

It catalyzes a variety of reactions including Michael reactions, Henry reactions, transesterification reactions, and Knoevenagel condensations.[7]

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

The conjugate acid of TBD is the preferred cation among the guanidinium hypoiodites, which are specialized oxidizing agents for various types of organic compounds.[8]

See also

Notes

  1. [1]
    Reaction specs:

References

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