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Merck

345571

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24861334
EC Number:
227-367-1
Beilstein/REAXYS Number:
3242
MDL number:
MFCD00043003

Key Documents

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Product Name

1,5,7-Triazabicyclo[4.4.0]dec-5-ene, 98%

InChI key

FVKFHMNJTHKMRX-UHFFFAOYSA-N

InChI

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

SMILES string

C1CNC2=NCCCN2C1

assay

98%

form

crystals

mp

125-130 °C (lit.)

solubility

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

Quality Level

200

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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.

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3494
BCBZ9044
BCBW4371
BCBW2494
BCBV5937

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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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