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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

Related Categories

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

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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

ALD00108-VAR:
ALD00108-1G:
ALD00108-100MG:
ALD00108-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.

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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.

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