MilliporeSigma
All Photos(1)

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
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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This Item
334718.03603136581
assay

98%

assay

≥98.0% (GC)

assay

≥97.0% (GC)

assay

98%

form

crystals

form

liquid

form

liquid

form

liquid

mp

125-130 °C (lit.)

mp

-

mp

-

mp

-

solubility

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

solubility

-

solubility

-

solubility

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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

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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