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

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
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 divinylbenzene
Packaging: 5G
Price: $186
Updated: 2024/03/01

Sigma-Aldrich

Product number: 345571
Product name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
Purity: 98%
Packaging: 5g
Price: $78.8
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

TCI Chemical

Product number: T1982
Product name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
Purity: >98.0%(HPLC)(T)
Packaging: 5g
Price: $92
Updated: 2024/03/01

TCI Chemical

Product number: T1982
Product name: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
Purity: >98.0%(HPLC)(T)
Packaging: 25g
Price: $347
Updated: 2024/03/01

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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].

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

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

Hebei Weibang Biotechnology Co., Ltd

Product: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 5807-14-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-31

Hebei Yanxi Chemical Co., Ltd.

Product: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 5807-14-7
Price: US $20.00-1.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 5 tons
Release date: 2023-11-06

Hebei Fengjia New Material Co., Ltd

Product: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene 5807-14-7
Price: US $30.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 100 tons
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

5807-14-7

5087-14-7

AMINE

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Synthetic Reagents

Pyrimidines

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Organic Bases

N-Containing

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N-Containing

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Chemical Synthesis

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