ALD00108
3,6-Bis(methylthio)-1,2,4,5-tetrazine
≥95% (HPLC)
Synonym(s):
3,6-Bis(methylthio)-s-tetrazine, NSC 674352, s-Tetrazine
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About This Item
Empirical Formula (Hill Notation):
C4H6N4S2
CAS Number:
Molecular Weight:
174.25
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
≥95% (HPLC)
Form:
powder
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:
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Articles
Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.
Related Content
Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| ALD00108-100MG | 04061833244661 |
| ALD00108-1G | 04061826656266 |