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345571

Sigma-Aldrich

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

98%

Synonym(s):

1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, Hhpp, TBD

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About This Item

Empirical Formula (Hill Notation):
C7H13N3
CAS Number:
5807-14-7
Molecular Weight:
139.20
Beilstein:
3242
EC Number:
227-367-1
MDL number:
MFCD00043003
UNSPSC Code:
12352100
PubChem Substance ID:
24861334
NACRES:
NA.22

Assay

98%

form

crystals

mp

125-130 °C (lit.)

solubility

acetonitrile: soluble
ethanol: soluble
organic solvents: soluble
water: soluble

SMILES string

C1CNC2=NCCCN2C1

InChI

1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)

InChI key

FVKFHMNJTHKMRX-UHFFFAOYSA-N

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General description

1,5,7-Triazabicyclo[4.4.0]dec-5-ene, a bicyclic guanidine base, has been found to be an excellent catalyst for Michael and Michael-type reactions. It forms 1:1 complex with lasalocid acid and crystal structure of the complex has been studied by X-ray diffraction, FT-IR spectroscopy and 1H NMR.

Application

1,5,7-Triazabicyclo[4.4.0]dec-5-ene may be used as organocatalyst for aminolysis of esters. It may be used as catalyst for direct addition of P(O)-H bonds (dialkyl phosphites and diphenyl phosphonite) across various activated alkenes. Polymer supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PTBD) was used as a base and a reagent scavenger for the synthesis of aryl ethers from phenols and alkyl or aryl halides.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jinfeng Wang et al.
Journal of surgical oncology, 111(8), 992-999 (2015-05-16)
We aimed to investigate potential of urinary cell-free microRNA-214 (miR-214) as a noninvasive biomarker for bladder cancer in this report. We screened miR-214 expression in medium from 2 bladder cancer cell lines to determine whether it is secretory. Then we
1, 5, 7-Triazabicyclo [4.4. 0] dec-5-ene (TBD) catalyzed Michael reactions.
Ye W, et al.
Tetrahedron Letters, 46(40), 6875-6878 (2005)
P-C Bond formation via direct and three-component conjugate addition catalyzed by 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene (TBD).
Jiang Z, et al.
Tetrahedron Letters, 48(1), 51-54 (2007)
Structural and spectroscopic studies of the 1: 1 complex of lasalocid acid with 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene.
Huczynski A, et al.
Journal of Molecular Structure, 875(1), 501-508 (2008)
A convenient aminolysis of esters catalyzed by 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene (TBD) under solvent-free conditions.
Sabot C, et al.
Tetrahedron Letters, 48(22), 3863-3866 (2007)
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