MilliporeSigma
All Photos(1)

345571

Sigma-Aldrich

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

98%

Synonym(s):
Hhpp, 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, TBD
Empirical Formula (Hill Notation):
C7H13N3
CAS Number:
Molecular Weight:
139.20
Beilstein:
3242
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Packaging

5 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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