| Identification | More | [Name]
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE | [CAS]
5807-14-7 | [Synonyms]
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE, POLYMER-BOUND
1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE
LABOTEST-BB LT00847641
TBD
2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-
1,5,7-Triazabicylo[4.4.0]dec-5-ene
Silicagel, functionalized, 1,5,7-Triazabicyclo[4,4,0]dec-5-ene, 1.4
1,5,7-TRIAZABICYCLO(4.4.0)DEC-5-ENE (1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO(1,2-A)PYRIMIDINE)
Hhpp, TBD, 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine
1,2,3,4,4a,5,6,7-Octahydro-1,4a,8-triazanaphthalene
1,2,3,4,7,8-Hexahydro-6H-pyrimido[1,2-a]pyrimidine
1,2,3,5,6,7-Hexahydro-4H-1,4a,8-triazanaphthalene
1,5,7-Triazabicyclo[4.4.0]decane-5-ene
2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine
1,5,7-Triazabicyclo(4 x 4 x 0)dec-5-ene (1,3,4,6,7,8-Hexahydro-2 | [EINECS(EC#)]
227-367-1 | [Molecular Formula]
C7H13N3 | [MDL Number]
MFCD00043003 | [Molecular Weight]
139.2 | [MOL File]
5807-14-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
125-130 °C(lit.)
| [Boiling point ]
222.3±23.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
toluene: soluble1 g/15 mL | [form ]
powder to crystal | [pka]
14.47±0.20(Predicted) | [color ]
White to Almost white | [Water Solubility ]
acetonitrile: soluble
ethanol: soluble
organic solvents: soluble
water: soluble | [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 DataBase Reference]
5807-14-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 1759 8/PG 2
| [WGK Germany ]
3
| [F ]
9-21-34 | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Description]
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]. | [Chemical Properties]
Light yellow crystalline | [Uses]
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. | [Definition]
ChEBI: 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine is a member of pyrimidines. | [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. | [Reactivity Profile]
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is a strong bicyclic guanidine base with a pKa = 24.97. It has been shown to promote various reactions, including the Horner–Wadsworth–Emmons reactions, nitroaldol (Henry) reaction, secondary amine alkylation, carboxylation of propylene glycol with CO2, Michael reactions, synthesis of symmetrically N, N′-substituted ureas, 5- and 6-enolexo aldolisation of acyclic ketoaldehydes, intramolecular aldolization of acyclic ketoaldehydes etc. In these reactions, TBD shows good activity and selectivity[3].
| [reaction suitability]
reaction type: solution phase peptide synthesis
reactivity: proton reactive | [Purification Methods]
It 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.] | [References]
[1] Chunling Blue Lan, Prof. Karine Auclair. “1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD): An Organocatalyst for Rapid Access to 3-Hydroxyisoindolin-1-ones.” European Journal of Organic Chemistry 27 12 (2024).
[2] Weiping Ye. “1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed Michael reactions.” Tetrahedron Letters 46 40 (2005): Pages 6875-6878.
[3] Iuliana Cota . “1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) an efficient homogeneous catalyst for aldol condensation reactions. Study of the catalyst recovery and reusability using CO2.” Tetrahedron Letters 52 3 (2011): Pages 385-387. |
|
|