Triazabicyclodecene

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:94622;
ChemSpider	72164 ;
ECHA InfoCard	100.024.880
EC Number	227-367-1;
PubChem CID	79873;
UNII	KAF7GN82TM ;
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) Key: FVKFHMNJTHKMRX-UHFFFAOYSA-N ; 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 (pKa)	15.2 ± 1.0 (pKa of conjugate acid in water); 26.03 (pKa 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 ?) Infobox references

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]

^ 1,5,7-Triazabicyclo[4.4.0]dec-5-ene at Sigma-Aldrich
^ 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.
^ 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.
^ 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.

[1] 1,5,7-Triazabicyclo[4.4.0]dec-5-ene at Sigma-Aldrich

[Kaupmees_CCA-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.

[Kaljurand_2005_JOC-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.

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