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Merck

ALD00108

Sigma-Aldrich

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

≥95% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C4H6N4S2
Número de CAS:
Peso molecular:
174.25
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95% (HPLC)

form

powder

mp

82-87 °C

storage temp.

−20°C

SMILES string

CSC1=NN=C(SC)N=N1

InChI

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

InChI key

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.

related product

Referencia del producto
Descripción
Precios

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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)
Triphenylamine/tetrazine based ?-conjugated systems as molecular donors for organic solar cells
Quinton C, et al.
New. J. Chem., 39(12), 9700-9713 (2015)
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)

Artículos

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

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

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

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

Contenido relacionado

Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.

Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.

Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.

Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.

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