1,5,7-Triazabicyclo[4.4.0]dec-5-ene
![1,5,7-Triazabicyclo[4.4.0]dec-5-ene Structure](CAS/GIF/5807-14-7.gif)
- CAS No.
- 5807-14-7
- Chemical Name:
- 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
- Synonyms
- TBD;1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE;1,5,7-Triazabicylo[4.4.0]dec-5-ene;2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-;Hhpp;129727;CATALYST TBD;o[4.4.0]dec-5-ene;1,5,7-TriazabicycL;Triazabicyclodecene
- CBNumber:
- CB4390305
- Molecular Formula:
- C7H13N3
- Molecular Weight:
- 139.2
- MOL File:
- 5807-14-7.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/11 15:28:25
Melting point | 125-130 °C(lit.) |
---|---|
Boiling point | 222.3±23.0 °C(Predicted) |
Density | 1.28±0.1 g/cm3(Predicted) |
storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
solubility | toluene: soluble1 g/15 mL |
pka | 14.47±0.20(Predicted) |
form | powder to crystal |
color | 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 DataBase Reference | 5807-14-7(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS05 |
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Signal word | Danger | |||||||||
Hazard statements | H314 | |||||||||
Precautionary statements | P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338 | |||||||||
Hazard Codes | C | |||||||||
Risk Statements | 34 | |||||||||
Safety Statements | 26-36/37/39-45-27 | |||||||||
RIDADR | UN 1759 8/PG 2 | |||||||||
WGK Germany | 3 | |||||||||
F | 9-21-34 | |||||||||
HazardClass | 8 | |||||||||
PackingGroup | III | |||||||||
HS Code | 29335990 | |||||||||
NFPA 704 |
|
1,5,7-Triazabicyclo[4.4.0]dec-5-ene price More Price(6)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich(India) | 358754 | 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound 200-400?mesh, extent of labeling: 2.6?mmol/g loading, 2?% cross-linked with divinylbenzene | 5807-14-7 | 1G | ₹2468.1 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 358754 | 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound 200-400?mesh, extent of labeling: 2.6?mmol/g loading, 2?% cross-linked with divinylbenzene | 5807-14-7 | 5G | ₹8887.33 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 358754 | 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound 200-400?mesh, extent of labeling: 2.6?mmol/g loading, 2?% cross-linked with divinylbenzene | 5807-14-7 | 25G | ₹35495.18 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | 345571 | 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 98% | 5807-14-7 | 5G | ₹5813.03 | 2022-06-14 | Buy |
TCI Chemicals (India) | T1982 | 1,5,7-Triazabicyclo[4.4.0]dec-5-ene | 5807-14-7 | 5G | ₹5000 | 2022-05-26 | Buy |
1,5,7-Triazabicyclo[4.4.0]dec-5-ene Chemical Properties,Uses,Production
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.
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].
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.]
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.
1,5,7-Triazabicyclo[4.4.0]dec-5-ene Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | Inquiry |
---|---|---|---|---|---|
ALTRAKEM PHARMA LIFE SCIENCES PRIVATE LIMITED | +919966658228 | Hyderabad, India | 486 | 58 | Inquiry |
SURVIVAL TECHNOLOGIES LIMITED | +91 8108285261 | Gujarat, India | 294 | 58 | Inquiry |
REAX CHEMICALS | +91-9347443900 +91-9347443900 | Hyderabad, India | 169 | 58 | Inquiry |
Suven Pharmaceuticals Limited | +91-91-40-23541142 +91-4023541142 | Telangana, India | 218 | 58 | Inquiry |
PVR Life Sciences | +91-9393797870 +91-9000984800 | Telangana, India | 38 | 58 | Inquiry |
OCEAN TRADING CORPORATION | +91(22) 24921669 | New Delhi, India | 6211 | 58 | Inquiry |
Venkateshwara Life Sciences | +91 9963894542 | New Delhi, India | 88 | 50 | Inquiry |
TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
Bharavi Laboratories (P) Ltd. | 91 80 2666 7742 | New Delhi, India | 359 | 54 | Inquiry |
Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
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