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Principaux documents

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ALD00108

Sigma-Aldrich

3,6-Bis(methylthio)-1,2,4,5-tetrazine

≥95% (HPLC)

Synonyme(s) :

3,6-Bis(methylthio)-s-tetrazine, NSC 674352, s-Tetrazine

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About This Item

Formule empirique (notation de Hill):
C4H6N4S2
Numéro CAS:
1672-34-0
Poids moléculaire :
174.25
Numéro MDL:
MFCD02998583
Code UNSPSC :
12352100
ID de substance PubChem :
329772592
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

powder

Pf

82-87 °C

Température de stockage

−20°C

Chaîne SMILES 

CSC1=NN=C(SC)N=N1

InChI

1S/C4H6N4S2/c1-9-3-5-7-4(10-2)8-6-3/h1-2H3

Clé InChI

ROUDTSAXQIBBFZ-UHFFFAOYSA-N

Application

3,6-Bis(methylthio)-1,2,4,5-tetrazine can be used as a versatile building block in the inverse elecron demand hetero Diels-Alder reactions. The Boger Research Group has reported this powerful approach in the synthesis of alkaloids.
It can also used to synthesize:
  • Substituted indoles and indolines derivatives by sequential [4+2] cycloaddition reactions.
  • 3-(Methylthio)-6-(4-morpholinyl)-1,2,4,5-tetrazine by aromatic nucleophilic substitution reaction.

Autres remarques

Total Synthesis of Amaryllidaceae Alkaloids Utilizing Sequential Intramolecular Heterocyclic Azadiene Diels-Alder Reactions of an Unsymmetrical 1, 2, 4, 5-Tetrazin
Regioselective Inverse Electron Demand Diels-Alder Reactions of N-Acyl 6-Amino-3-(methylthio)-1, 2, 4, 5-tetrazines

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000193903
MKBX4007V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Triphenylamine/tetrazine based ?-conjugated systems as molecular donors for organic solar cells
Quinton C, et al.
New. J. Chem., 39(12), 9700-9713 (2015)
Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels- Alder reactions of an unsymmetrical 1, 2, 4, 5-tetrazine
Boger DL and Wolkenberg SE
The Journal of Organic Chemistry, 65(26), 9120-9124 (2000)
3, 6-Diphenyl-1, 2, 4, 5-tetrazine
Boger DL, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 65(26), 9120-9124 (2001)

Articles

Inverse Electron Demand Diels-Alder Reactions

Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.

Inverse Electron Demand Diels-Alder Reactions

Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.

Inverse Electron Demand Diels-Alder Reactions

Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.

Inverse Electron Demand Diels-Alder Reactions

Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.

Contenu apparenté

Boger Group – Professor Product Portal

As the exploration of the properties of complex natural products becomes increasingly more sophisticated with the technological advances being made in their screening and evaluation and as structural details of their interaction with biological targets becomes more accessible, the importance and opportunities for providing unique solutions to complex biological problems has grown. The Boger Lab addresses these challenging problems by understanding the complex solutions and subtle design elements that nature has provided in the form of a natural product and work to extend the solution through rational design elements to provide more selective, more efficacious, or more potent agents designed specifically for the problem or target under investigation. The resulting efforts have reduced many difficult or intractable synthetic challenges to manageable problems providing an approach not only to the natural product but one capable of simple extrapolation to a series of structural analogs with improved selectivity and efficacy.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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