Triazabicyclodecene

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^[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

CAS Number

5807-14-7^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:94622

ChemSpider

72164^Y

ECHA InfoCard

100.024.880

EC Number

227-367-1

PubChem CID

79873

UNII

KAF7GN82TM^Y

CompTox Dashboard (EPA)

DTXSID10206793

InChI

InChI=1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)^Y
Key: FVKFHMNJTHKMRX-UHFFFAOYSA-N^Y
InChI=1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
Key: FVKFHMNJTHKMRX-UHFFFAOYAP

SMILES

N\2=C1/NCCCN1CCC/2

Properties

Chemical formula

C₇H₁₃N₃

Molar mass

139.20 g/mol

Melting point

125 to 130 °C (257 to 266 °F; 398 to 403 K)

Acidity (pK_a)

15.2 ± 1.0^[2] (pK_a of conjugate acid in water); 26.03^[3] (pK_a of conjugate acid in acetonitrile)

Hazards

GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H314

Precautionary statements

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).

verify (what is ^YN ?)

Infobox references

Close

Reactivity

As a strong base, TBD fully deprotonates most phenols, carboxylic acids, and some carbon acids.^[7] It catalyzes a variety of reactions including Michael reactions, Henry 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).

The conjugate acid of TBD is the preferred cation among the guanidinium hypoiodites, which are specialized oxidizing agents for various types of organic compounds.^[9]

References

[1]
1,5,7-Triazabicyclo[4.4.0]dec-5-ene at Sigma-Aldrich
[2]
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.
[3]
Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pK_a Units: Unification of Different Basicity Scales". J. Org. Chem. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
[4]
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.
[5]
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.
[6]
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
[7]
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.
[8]
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.
[9]
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.

Triazabicyclodecene

Reactivity

See also

References

Related Articles