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

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

Product Name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
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
Formula Weight: 139.2
MOL File: 5807-14-7.mol

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

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
form: powder to crystal
pka: 14.47±0.20(Predicted)
color: White to Almost white
Water Solubility: acetonitrile: soluble
ethanol: soluble
organic solvents: soluble
water: soluble
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)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 358754
Product name: 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound
Purity: 200-400 mesh, extent of labeling: 2.6 mmol/g loading, 2 % cross-linked with divinylbe
Packaging: 1 g
Price: $58
Updated: 2025/07/31

Sigma-Aldrich

Product number: 358754
Product name: 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound
Purity: 200-400 mesh, extent of labeling: 2.6 mmol/g loading, 2 % cross-linked with divinylbe
Packaging: 5 g
Price: $192
Updated: 2025/07/31

Sigma-Aldrich

Product number: 345571
Product name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
Purity: 98%
Packaging: 5g
Price: $81.2
Updated: 2025/07/31

Sigma-Aldrich

Product number: 358754
Product name: 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound
Purity: 200-400?mesh, extent of labeling: 2.6?mmol/g loading, 2?% cross-linked with divinylbenzene
Packaging: 5G
Price: $186
Updated: 2024/03/01

Sigma-Aldrich

Product number: 358754
Product name: 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine, polymer-bound
Packaging: 25g
Price: $648
Updated: 2023/06/20

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1,5,7-Triazabicyclo[4.4.0]dec-5-ene Chemical Properties,Usage,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].

reaction suitability

reaction type: solution phase peptide synthesis
reactivity: proton reactive

Synthesis

56-18-8

50-01-1

5807-14-7

To a 100 mL autoclave equipped with a reflux condenser and an electric stirrer, 20 mL of aqueous GHC (6.0 mmol/mL) and 20 mL (5.0 mmol/mL) of APA solution in homotrimethylbenzene were added, as well as 0.578 g of pretreated atmospheric anion-exchange resin (D201).The reaction was carried out under argon gas protection for 9 h at 120°C. The reaction was completed by filtration. Upon completion of the reaction, the D201 resin in the reaction mixture was first recovered by filtration (the washed and dried recovered resin was used to repeat the synthesis experiments). Subsequently, the oil-water system was filtered, and the homotrimethylbenzene in the oil phase was separated and recovered using a partition funnel. The aqueous phase was distilled to yield a pale yellow viscous liquid, which was extracted with 30 mL of dichloromethane. Dichloromethane was recovered by distillation through rotary evaporator. The resulting colorless oily liquid was placed in a freezer at 12°C for 12 hours and then allowed to stand at room temperature (15 to 25°C), gradually converting to a pale yellow solid. Finally, it was dried under vacuum at 40°C for 40 h to afford 1,5,7-triazabicyclo[4.4.0]decen-5-ene (TBD) 7.66 g in 55% yield.

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

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Shaanxi Dideu New Materials Co. Ltd

Product: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 5807-14-7
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98
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ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

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Hebei Fengjia New Material Co., Ltd

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Release date: 2024-08-09

5807-14-7, 1,5,7-Triazabicyclo[4.4.0]dec-5-eneRelated 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

LABOTEST-BB LT00847641

1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE

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

TBD

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-

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

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

129727

1,5,7-TriazabicycL

o[4.4.0]dec-5-ene

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

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-h

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

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-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

1H,2H,3H,4H,6H,7H,8H-[1,3]diazino[1,2-a]pyrimidine - [H4641]

1,5,7-Triazabicyclo[4.4.0]dec-5-ene(TBD)

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