Triazabicyclodecene

chembox new
Reference= [ [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/345571?cm_mmc=PubChem-_-public%20database-_-products-_-products 1,5,7-Triazabicyclo [4.4.0] dec-5-ene] at Sigma-Aldrich]
ImageFileL1=TBD.pngImageSizeL1=120px
ImageFileR1=TBD 2.pngImageSizeR1=120px
IUPACName=3,4,6,7,8,9-Hexahydro-2"H"-pyrimido [1,2-a] pyrimidine
OtherNames=
Section1=Chembox Identifiers
CASNo=5807-14-7
PubChem=79873
SMILES=C1CNC2=NCCCN2C1
Section2=Chembox Properties
Formula=C₇H₁₃N₃
MolarMass=139.20 g/mol
Appearance=
Density=
MeltingPt=125-130 °C
BoilingPt=
Solubility=
Section3=Chembox Hazards
MainHazards=
FlashPt=
Autoignition=
SPhrases = S26 S36/37/39 S45
RPhrases = R34

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 [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] :
* 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