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ALD00108

Sigma-Aldrich

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:
1672-34-0
Molecular Weight:
174.25
MDL number:
MFCD02998583
UNSPSC Code:
12352100
PubChem Substance ID:
329772592
NACRES:
NA.22

Quality Level

100

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.

Other Notes

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

related product

Product No.
Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBX4007V

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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)

Articles

Inverse Electron Demand Diels–Alder Reactions of 1,2,4,5-Tetrazines and 1,2,3-Triazines

The inverse electron demand Diels-Alder reactions of electron-deficient heterocycles are significant cycloaddition reactions for the total synthesis of natural products containing highly substituted and functionalized heteroaromatic ring systems.

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