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

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.

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges