1,5,7-Triazabicyclo[4.4.0]dec-5-ene
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene ??
- ???
- 125-130 °C(lit.)
- ?? ?
- 222.3±23.0 °C(Predicted)
- ??
- 1.28±0.1 g/cm3(Predicted)
- ?? ??
- under inert gas (nitrogen or Argon) at 2–8 °C
- ???
- ???: ???1 g/15 mL
- ??? ??
- powder to crystal
- ?? ?? (pKa)
- 14.47±0.20(Predicted)
- ??
- ???? ?? ??
- BRN
- 3242
- InChI
- InChI=1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
- InChIKey
- FVKFHMNJTHKMRX-UHFFFAOYSA-N
- SMILES
- C12=NCCCN1CCCN2
- CAS ??????
- 5807-14-7(CAS DataBase Reference)
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- ?? ? ?? ??
- ?? ? ???? ?? (GHS)
| ??? ?? | C | ||
|---|---|---|---|
| ?? ???? ?? | 34 | ||
| ????? | 26-36/37/39-45-27 | ||
| ????(UN No.) | UN 1759 8/PG 2 | ||
| WGK ?? | 3 | ||
| F ?????? | 9-21-34 | ||
| ?? ?? | 8 | ||
| ???? | III | ||
| HS ?? | 29335990 | ||
| ???? ?? | 2015-3-6870 |
1,5,7-Triazabicyclo[4.4.0]dec-5-ene C??? ??, ??, ??
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is a bicyclic guanidine that has found extensive application in organic chemistry, notably as a powerful catalyst for polymer synthesis and recycling, CO2 utilization, and carboxylic acid derivative synthesis. Bearing both a nucleophilic nitrogen and an electrophilic N?H group, TBD is a multifunctional reagent. It can serve as an organic superbase, an acyl transfer reagent, and a hydrogen bonding activator. It is an excellent catalyst for Michael and Michael-type reactions. The readily available organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the rapid synthesis of 3-hydroxyisoindolin-1-ones from 3-alkylidenephthalides[1-2].??? ??
Light yellow crystalline??
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.?? ??
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.Purification Methods
1,5,7-Triazabicyclo[4.4.0]dec-5-ene crystallises from Et2O but readily forms white crystals of the carbonate. It is a strong base (see pK, i.e. about 100 times more basic than tetramethylguanidine). The picrate has m 220.5-222o (from EtOH). It forms the 5-nitro derivative m 14.5-160o that gives a 5-nitro nitrate salt m 100-101o (from EtOH/Et2O) and a 5-nitro picrate m 144-145o (from H2O) [McKay & Kreling Can J Chem 35 1438 1957, Schwesinger Chimia 39 369 1985, Hilpert et al. J Chem Soc, Chem Commun 1401 1983, Kamfen & Eschenmoser Helv Chim Acta 72 185 1989]. [Beilstein 26 III/IV 60.]1,5,7-Triazabicyclo[4.4.0]dec-5-ene ?? ?? ? ???
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene ?? ??
???( 289)?? ??
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene ?? ??:
Tributyltin azide
Tetramethylguanidine
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-ALPHA]PYRIMIDINE POLYMER BOUND
JANDAJEL-1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO-(1,2A)PYRIMIDINE
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE BOUND TO POLYSTYRENE
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE RESIN
1,5,7-Triazabicyclo[4.4.0]dec-5-ene
1-Methyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine,1-Methyl-1,2,3,4,7,8-hexahydro-6H-pyrimido[1,2-a]pyrimidine
AURORA KA-6614
AURORA KA-6611
AURORA KA-6613
AURORA KA-6612