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ChemicalBook >> CAS DataBase List >>1,5,7-Triazabicyclo[4.4.0]dec-5-ene

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

1,5,7-Triazabicyclo[4.4.0]dec-5-ene Structure
1,5,7-Triazabicyclo[4.4.0]dec-5-ene structure
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
MDL Number:
MFCD00043003
MOL File:
5807-14-7.mol
MSDS File:
SDS
Last updated:2024-11-15 19:19:13
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1,5,7-Triazabicyclo[4.4.0]dec-5-ene Properties

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)
FDA UNII KAF7GN82TM

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
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
0
3 0

1,5,7-Triazabicyclo[4.4.0]dec-5-ene price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 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 $186 2024-03-01 Buy
Sigma-Aldrich 345571 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 98% 5807-14-7 5g $78.8 2024-03-01 Buy
Sigma-Aldrich 358754 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound 5807-14-7 25g $648 2023-06-20 Buy
TCI Chemical T1982 1,5,7-Triazabicyclo[4.4.0]dec-5-ene >98.0%(HPLC)(T) 5807-14-7 5g $92 2024-03-01 Buy
TCI Chemical T1982 1,5,7-Triazabicyclo[4.4.0]dec-5-ene >98.0%(HPLC)(T) 5807-14-7 25g $347 2024-03-01 Buy
Product number Packaging Price Buy
358754 5G $186 Buy
345571 5g $78.8 Buy
358754 25g $648 Buy
T1982 5g $92 Buy
T1982 25g $347 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.

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].

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

1,5,7-Triazabicyclo[4.4.0]dec-5-ene Suppliers

Global( 288)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai Jinhuan Chemical CO.,LTD.
+86-21-52210535 +8613162045318 sales@jinhchem.com China 331 58
Beri Pharma Co., Ltd.
+8613417710166 sales@zhberi.com China 227 58
Hebei Mojin Biotechnology Co., Ltd 		+86 13288715578 +8613288715578 sales@hbmojin.com China 12839 58
Hebei Yanxi Chemical Co., Ltd. 		+8617531190177 peter@yan-xi.com China 5857 58
Hebei Fengjia New Material Co., Ltd 		+86-0311-87836622 +86-17333973358 sales06@hbduling.cn China 8053 58
Hebei Weibang Biotechnology Co., Ltd 		+8617732866630 bess@weibangbio.com China 18153 58
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3009 60
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29881 58
NINGBO INNO PHARMCHEM CO., LTD. 		13867897135 sales@nbinno.com CHINA 923 58
Supplier Advantage
Shanghai Jinhuan Chemical CO.,LTD.
58
Beri Pharma Co., Ltd.
58
Hebei Mojin Biotechnology Co., Ltd 		58
Hebei Yanxi Chemical Co., Ltd. 		58
Hebei Fengjia New Material Co., Ltd 		58
Hebei Weibang Biotechnology Co., Ltd 		58
Henan Tianfu Chemical Co.,Ltd. 		55
Nanjing ChemLin Chemical Industry Co., Ltd. 		60
career henan chemical co 		58
NINGBO INNO PHARMCHEM CO., LTD. 		58

View Lastest Price from 1,5,7-Triazabicyclo[4.4.0]dec-5-ene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
1,5,7-Triazabicyclo[4.4.0]dec-5-ene pictures 2024-11-15 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
5807-14-7
 US $20.00 / g 10g TargetMol Chemicals Inc.
1,5,7-Triazabicyclo[4.4.0]dec-5-ene pictures 2024-10-31 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
5807-14-7
 US $0.00 / KG 1KG 99% 500000kg Hebei Weibang Biotechnology Co., Ltd
1,5,7-Triazabicyclo[4.4.0]dec-5-ene pictures 2024-10-25 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
5807-14-7
 US $20.00-1.00 / kg 1kg 0.99 5 tons Hebei Yanxi Chemical Co., Ltd.

1,5,7-Triazabicyclo[4.4.0]dec-5-ene Spectrum

1,5,7-Triazabicyclo[4.4.0]dec-5-ene(5807-14-7)1HNMR1,5,7-Triazabicyclo[4.4.0]dec-5-ene(5807-14-7)IR1,5,7-Triazabicyclo[4.4.0]dec-5-ene(5807-14-7)Raman

5807-14-7(1,5,7-Triazabicyclo[4.4.0]dec-5-ene)Related Search:

Tributyltin azide Tetramethylguanidine 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-ALPHA]PYRIMIDINE POLYMER BOUND JANDAJEL-1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO-(1,2A)PYRIMIDINE 1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE BOUND TO POLYSTYRENE
1,3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE RESIN 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 1-Methyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine,1-Methyl-1,2,3,4,7,8-hexahydro-6H-pyrimido[1,2-a]pyrimidine AURORA KA-6614 AURORA KA-6611
AURORA KA-6613 AURORA KA-6612

1of3

LABOTEST-BB LT00847641 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 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 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 Hhpp 1H,2H,3H,4H,6H,7H,8H-[1,3]diazino[1,2-a]pyriMidine 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine TBD 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine 3,4,6,7,8-HEXAHYDRO-2H-PYRIMIDO[1,2-A]PYRIMIDINE 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 98% StratoSpheres? PL-TBD (1,3,5-Triazabicyclodec-5-ene) resin 129727 1,5,7-TriazabicycL o[4.4.0]dec-5-ene 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-h 1,5,7-Triazabicyclo[4.4.0]dec-5-ene > 1,5,7-Triazabicyclo[4.4.0]dec-5-ene, 98%, for synthesis 1,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine CATALYST TBD 1,5,7-Triazabicyclo[4.4.]dec-5-ene 1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE TBD 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- 1,5,7-Triazabicylo[4.4.0]dec-5-ene 1,5, 7-triazicycle [4.4.0] dec-5-ene 1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, TBD Triazabicyclodecene 5807-14-7 5087-14-7 AMINE Heterocyclic Building Blocks Synthetic Reagents Pyrimidines Others Organic Bases N-Containing Building Blocks N-Containing Others Building Blocks Chemical Synthesis Heterocyclic Building Blocks