Triazabicyclodecene

Triazabicyclodecene^[1]

IUPAC name 3,4,6,7,8,9-Hexahydro-2H-pyrimido[1,2-a]pyrimidine
Identifiers
CAS number	5807-14-7
PubChem	79873
ChemSpider	72164^Y
Jmol-3D images	Image 1
SMILES N\2=C1/NCCCN1CCC/2
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
Properties
Molecular formula	C₇H₁₃N₃
Molar mass	139.20 g/mol
Melting point	125-130 °C
Hazards
R-phrases	R34
S-phrases	S26 S36/37/39 S45
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triazabicyclodecene (1,5,7-Triazabicyclo[4.4.0]dec-5-ene or TBD) is a commercially available bicyclic strong guanidine base (pKa = 25.98 in CH₃CN and pKa = 21.00 in THF). TBD is an organic soluble base which has been used effectively for a variety of base-mediated organic transformations such as:^[2]

Michael reactions,
Henry (nitroaldol reactions),
Wittig reactions,
Horner-Wadsworth-Emmons reactions,
transesterification reactions,
etherifications,
ring-opening polymerizations (Scheme 1),
tautomerizations and epimerizations
P-C and P-N bond formations,
Knoevenagel condensations,
deprotonation reactions of phenols, carboxylic acids and C-acids (Scheme 2)

References

^ 1,5,7-Triazabicyclo[4.4.0]dec-5-ene at Sigma-Aldrich
^ Adam Huczynski, Bogumil Brzezinski, "1,5,7-Triazabicyclo[4.4.0]dec-5-ene", e-EROS Encyclopedia of Reagents for Organic Synthesis,John Wiley & Sons, Ltd 2008,doi:10.1002/047084289X.rn00786
^ Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters Russell C. Pratt, Bas G. G. Lohmeijer, David A. Long, Robert M. Waymouth, and James L. Hedrick J. Am. Chem. Soc.; 2006; 128(14) pp 4556 - 4557 Abstract
^ Reaction specs: initiator 4-pyrenebutanol (pyrene enables end-group determination by UV/VIS spectroscopy 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
^ A. Huczyński, I. Binkowska, A. Jarczewski, B. Brzezinski, "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", Journal of Molecular Structure, 841(1-3), 2007, 133-136, doi:10.1016/j.molstruc.2007.01.005