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345571

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

Name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
Brand: ALDRICH

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

Assay:

98%

Form:

crystals

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Properties

Quality Level

200

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

Description

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.

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A

signalword

Danger

Storage Class

8A - Combustible corrosive hazardous materials

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Polymer supported bases in combinatorial chemistry: synthesis of aryl ethers from phenols and alkyl halides and aryl halides.

Xu W, et al.

Tetrahedron Letters, 38(42), 7337-7340 (1997)

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)

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)

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Global Trade Item Number

SKU	GTIN
345571-5G	04061826760789