Triazabicyclodecene
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine | |||
Other names
| |||
| Identifiers | |||
3D model (JSmol) |
|||
| Abbreviations |
| ||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.024.880 | ||
| EC Number |
| ||
PubChem CID |
|||
| UNII | |||
| UN number | 1759 | ||
CompTox Dashboard (EPA) |
|||
| |||
| |||
| 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] | |||
  | |||
| 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) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |||
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]
Reactivity
[edit]
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
[edit]- 1,5-Diazabicyclo(4.3.0)non-5-ene (DBN), a structurally related strong base
- 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU), a structurally related strong base
- 7-Methyl-TBD, a methyl derivative of TBD
Notes
[edit]- ↑ Reaction specs:
- initiator: 4-pyrenebutanol (pyrene enables end-group determination by UV–vis) and
- Monomer: caprolactone added in ratio 1:100,
- Targeted degree of polymerization: 100
- With TBD cat. 0.5% in benzene.
- 72% conversion in 8 hours.
- Polydispersity index: 1.16[citation needed]
References
[edit]- 1 2 Sigma-Aldrich Co., 1,5,7-triazabicyclo[4.4.0]dec-5-ene.
- 1 2 3 4 5 "SDS - 1,5,7-Triazabicyclo(4.4.0)dec-5-ene" (PDF). cdn.caymanchemical.com. Cayman Chemical. 4 December 2025. p. 2. Retrieved 14 May 2026.
- ↑ Kaupmees, K.; Trummal, A.; Leito, I. (2014). "Basicities of Strong Bases in Water: A Computational Study". Croat. Chem. Acta. 87 (4): 385–395. doi:10.5562/cca2472.
- ↑ Huczynski, Adam; Brzezinski, Bogumil (2008). "1,5,7-Triazabicyclo[4.4.0]dec-5-ene". e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rn00786. ISBN 978-0-471-93623-7.
- ↑ Pratt, Russell C.; Lohmeijer, Bas G. G.; Long, David A.; Waymouth, Robert M.; Hedrick, James L. (2006). "Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters". J. Am. Chem. Soc. 128 (14): 4556–4557. Bibcode:2006JAChS.128.4556P. doi:10.1021/ja060662+. PMID 16594676.
- ↑ Huczyński, A.; Binkowska, I.; Jarczewski, A.; Brzezinski, B. (2007). "Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene". J. Mol. Struct. 841 (1–3): 133–136. Bibcode:2007JMoSt.841..133H. doi:10.1016/j.molstruc.2007.01.005.
- ↑ Sabot, Cyrille; Kumar, Kanduluru Ananda; Meunier, Stéphane; Mioskowski, Charles (2007). "A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions". Tetrahedron Lett. 48 (22): 3863–3866. doi:10.1016/j.tetlet.2007.03.146.
- ↑ Odagi, Miami; Nagasawa, Kazuo (2023). "Exploring Guanidinium Organocatalysts for Hypoiodite-Mediated Reactions". The Chemical Record. 23 (7) e202300030. doi:10.1002/tcr.202300030. PMID 36949010.
