1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidin
Triazabicyclodecene
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Grundinformationen
- CAS
5807-14-7- Standard-SMILES
C1CN=C2NCCCN2C1- InChIKey
FVKFHMNJTHKMRX-UHFFFAOYSA-N- Summenformel
- C7H13N3
- Durchschnittliche Molmasse
- 139,2 g/mol
- Monoisotopische Masse
- 139,11094743
Namen und Bezeichner
- Bevorzugter Name
- Triazabicyclodecene
- IUPAC
- 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine
- Lokaler Name
- 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidin
- Englischer Name
- 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
- Summenformel
- C7H13N3
- Molmasse
- 139.2
Namen und Synonyme
TriazabicyclodeceneKAF7GN82TMTBD compoundRefChem:9333185807-14-71,5,7-Triazabicyclo[4.4.0]dec-5-ene1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidineHhpp2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine1,3,4,6,7,8-Hexahydro-2H-pyrimido(1,2-a)pyrimidineMFCD00043003
Weitere Namen anzeigen
TBD1,5,7-TriazabicycL1,5,7-Triazabicylo[4.4.0]dec-5-ene129727
2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-1,5,7-triazabicyclo(4.4.0)dec-5-ene1H,2H,3H,4H,6H,7H,8H-[1,3]diazino[1,2-a]pyrimidine2H-Pyrimido(1,2-a)pyrimidine, 1,3,4,6,7,8-hexahydro-1,5,7-triazabicyclo [4.4.0]dec-5-ene5,6,7,8-tetrahydro-1H,2H,3H,4H-pyrimidino[1,2-a]1,3-diazaperhydroineTBD; 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,5,7-Triazabicyclo[4.4.0]deca-5-ene; 1,5,9-Triazabicyclo[4.4.0]dec-9-ene; 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine;EINECS 227-367-1
Datenbank-Bezeichner
- CAS
5807-14-7- PubChem CID
- 79873
- DTXSID
DTXSID10206793- ChEBI
CHEBI:94622- UNII
- KAF7GN82TM
- EC Number
- 227-367-1
- Nikkaji
- J218.068E
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -0,3
- Polarare Oberfläche (TPSA)
- 27,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 153
Experimentelle und physikochemische Eigenschaften
Physical DescriptionLiquid
Physikochemische Eigenschaften
- Schmelzpunkt
- 125 · 125-130 °C(lit.)
- Siedepunkt
- 222.3 · 222.3±23.0 °C(Predicted)
- Dichte
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- Löslichkeit
- 1 g/15 · toluene: soluble1 g/15 mL
- Aggregatzustand
- powder to crystal
- pka
- 14.47 · 14.47±0.20(Predicted)
- Farbe
- White to Almost white
- Wasserlöslichkeit
- acetonitrile: solubleethanol: solubleorganic solvents: solublewater: soluble
- BRN
- 3242 · 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 · 5807-14-7(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 27.7% (18 of 65) of reports.
Danger
H314 (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.
Gefahrenhinweise
Regulatory Information
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 CategoriesSkin Corr. 1A (72.3%)
Regulatorische Informationen
Regulatory Information
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
Sicherheitsdaten
- F
- 9-21-34
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1759 8/PG 2
- hs_code
- 29335990
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- Skin Corr. 1B
Chemie und Industrie
Verwendung und Herstellung
U.S. Production2023: 31,845 lb；2022: <50,000 lb；2021: <50,000 lb；2020: <50,000 lb
Industry UsesCatalyst
General Manufacturing Information
Paint and Coating Manufacturing
2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-: ACTIVE
Anwendungen
Beschreibung1,5,7-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].
Verwenden1,5,7-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.
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