:Triazabicyclodecene
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470613105
| Reference = [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/345571 1,5,7-Triazabicyclo[4.4.0]dec-5-ene] at Sigma-Aldrich
| ImageFileL1 = Triazabicyclodecene.svg
| ImageFileR1 = TBD 2.png
| PIN = 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine
| OtherNames = 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
TBD
Hexahydropyrimidopyrimidine
hpp
|Section1={{Chembox Identifiers
| ChEBI = 94622
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 72164
| EINECS = 227-367-1
| InChI = 1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
| InChIKey = FVKFHMNJTHKMRX-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FVKFHMNJTHKMRX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}| CASNo = 5807-14-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KAF7GN82TM
| PubChem = 79873
| SMILES = N\2=C1/NCCCN1CCC/2
}}
|Section2={{Chembox Properties
| Formula =C7H13N3
| MolarMass =139.20 g/mol
| Appearance =
| Density =
| MeltingPtC = 125 to 130
| MeltingPt_notes =
| BoilingPt =
| Solubility =
| pKa = 15.2 ± 1.0{{cite journal | last1 = Kaupmees | first1 = K. | last2 = Trummal | first2 = A. | last3 = Leito | first3 = I. | title = Basicities of Strong Bases in Water: A Computational Study | journal = Croat. Chem. Acta | year = 2014 | volume = 87 | issue = 4 | pages = 385–395 | doi = 10.5562/cca2472 | doi-access = free }} (pKa of conjugate acid in water); 26.03{{cite journal | last1 = Kaljurand | first1 = I. | last2 = Kütt | first2 = A. | last3 = Sooväli | first3 = L. | last4 = Rodima | first4 = T. | last5 = Mäemets | first5 = V. | last6 = Leito | first6 = I. | last7 = Koppel | first7 = I. A. | title = Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales | journal = J. Org. Chem. | year = 2005 | volume = 70 | issue = 3 | pages = 1019–1028 | doi = 10.1021/jo048252w | pmid=15675863}} (pKa of conjugate acid in acetonitrile)
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|314}}
| PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
}}
}}
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.{{cite encyclopedia|first1=Adam|last1=Huczynski|first2=Bogumil|last2=Brzezinski|title=1,5,7-Triazabicyclo[4.4.0]dec-5-ene|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley & Sons|date=2008|doi=10.1002/047084289X.rn00786|isbn=978-0-471-93623-7}}
Reactivity
Image:TBD caprolactonePolym.png of caprolactone to polycaprolactone by TBD.{{cite journal|title=Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters|first1=Russell C.|last1=Pratt|first2=Bas G. G.|last2=Lohmeijer|first3=David A.|last3=Long|first4=Robert M.|last4=Waymouth|first5=James L.|last5=Hedrick|journal=J. Am. Chem. Soc.|date=2006|volume=128|issue=14|pages=4556–4557|doi=10.1021/ja060662+|pmid=16594676|bibcode=2006JAChS.128.4556P }}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]]
As a strong base, TBD fully deprotonates most phenols, carboxylic acids, and some carbon acids.{{cite journal|first1=A.|last1=Huczyński|first2=I.|last2=Binkowska|first3=A.|last3=Jarczewski|first4=B.|last4=Brzezinski|title=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=J. Mol. Struct.|volume=841|issue=1–3|date=2007|pages=133–136|doi=10.1016/j.molstruc.2007.01.005|bibcode=2007JMoSt.841..133H }} It catalyzes a variety of reactions including Michael reactions, Henry reactions, transesterification reactions, and Knoevenagel condensations.{{cite journal|first1=Cyrille|last1=Sabot|first2=Kanduluru Ananda|last2=Kumar|first3=Stéphane|last3=Meunier|first4=Charles|last4=Mioskowski|title=A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions|journal=Tetrahedron Lett.|date=2007|volume=48|issue=22|pages=3863–3866|doi=10.1016/j.tetlet.2007.03.146}}
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.{{cite journal |doi= 10.1002/tcr.202300030 |title= Exploring Guanidinium Organocatalysts for Hypoiodite-Mediated Reactions |date= 2023 |last1= Odagi |first1= Miami |last2= Nagasawa |first2= Kazuo |journal= The Chemical Record |volume= 23 |issue= 7 |pages= e202300030 |pmid= 36949010 }}
See also
- 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