Basic information
- Standard SMILES
C1CN=C2NCCCN2C1- InChIKey
FVKFHMNJTHKMRX-UHFFFAOYSA-N- Molecular formula
- C7H13N3
- Average molar mass
- 139.2 g/mol
- Monoisotopic mass
- 139.11094743
Names & identifiers
- Preferred name
- Triazabicyclodecene
- IUPAC
- 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine
- English name
- 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
- Molecular formula
- C7H13N3
- Molecular weight
- 139.2
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
5807-14-7- PubChem CID
- 79873
- DTXSID
DTXSID10206793- ChEBI
CHEBI:94622- UNII
- KAF7GN82TM
- EC Number
- 227-367-1
- Nikkaji
- J218.068E
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 27.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 153
Experimental & physicochemical properties
Physical DescriptionLiquid
Physicochemical properties
- Melting point
- 125 · 125-130 °C(lit.)
- Boiling point
- 222.3 · 222.3±23.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- 1 g/15 · toluene: soluble1 g/15 mL
- form
- powder to crystal
- pka
- 14.47 · 14.47±0.20(Predicted)
- color
- White to Almost white
- Water Solubility
- 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 DataBase Reference
- 5807 · 5807-14-7(CAS DataBase Reference)
- FDA UNII
- 7 GN82TM · KAF7GN82TM
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 260 · P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 34 · 34
- Safety Statements
- 26 · 26-36/37/39-45-27
- RIDADR
- 1759 · UN 1759 8/PG 2
- WGK Germany
- 3 · 3
- F
- 9 · 9-21-34
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29335990 · 29335990
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 B · Skin Corr. 1B
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
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%)
Regulatory information
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
Safety data
- F
- 9-21-34
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1759 8/PG 2
- hs_code
- 29335990
- risk_code
- 34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H314
- REACH Registrations
- Active
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
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
Applications
Description1,5,7-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].
Uses1,5,7-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.
General Description1,5,7-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.
Upstream & downstream products
Upstream raw materials
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常州帝通化工有限公司+86-0519-88298848 · [email protected]
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Additional notes
DefinitionChEBI: 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine is a member of pyrimidines.
Related reactions
100 records
Linked notes
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