1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidin
TBD · 1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE · 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE · Triazabicyclodecene · 1,5,7-TriazabicycL · 1,5,7-Triazabicylo[4.4.0]dec-5-ene · 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine · 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-
![Molekülstruktur von 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidin](/img/chemical/79873.png)
Identifikatoren & physikalische Daten
| CAS No. | 5807-14-7 |
|---|---|
| Summenformel | C7H13N3 |
| Durchschnittliche Molmasse | 139,2 g/mol |
| Monoisotopische Masse | 139,11094743 g/mol |
| SMILES | C1CN=C2NCCCN2C1 |
| InChIKey | FVKFHMNJTHKMRX-UHFFFAOYSA-N |
| PubChem CID | 79873 |
| ChEBI | CHEBI:94622 |
| EC No. | 227-367-1 |
| DTXSID | DTXSID10206793 |
| Lokaler Name | 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidin |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 27,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 153 |
| Physical Description | Liquid |
| Schmelzpunkt | 125-130 °C(lit.) |
| Siedepunkt | 222.3±23.0 °C(Predicted) |
| Dichte | 1.28±0.1 g/cm3(Predicted) |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2–8 °C |
| Löslichkeit | toluene: soluble1 g/15 mLacetonitrile: solubleethanol: solubleorganic solvents: solublewater: soluble |
| Aggregatzustand | powder to crystal |
| pKa (Säurekonstante) | 14.47±0.20(Predicted) |
| Farbe | White to Almost white |
| 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 Datenbank | 5807-14-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 27.7% (18 of 65) of reports.DangerH314 (72.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 65 reports by companies from 6 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 18 of 65 reports by companies.There are 5 notifications provided by 47 of 65 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 05-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25177 |
| Hazard Classes and Categories | Skin Corr. 1A (72.3%) |
| F | 9-21-34 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1759 8/PG 2 |
| Zollcode | 29335990 |
| R-Sätze (R) | 34 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45-27 |
| Gefahrenklasse | 8Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
Anwendungen & Verwendung
Beschreibung
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 NH 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].
Verwenden
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.