3,6-Dimethyl-1,2,4,5-tetrazine

Name: 3,6-Dimethyl-1,2,4,5-tetrazine
Brand: ChemScene
Availability: InStock
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CAS No. 1558-23-2
Cat. No. CS-0512987
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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3,6-Dimethyl-1,2,4,5-tetrazine|CS-0512987

Structure of 1558-23-2

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General Information

CAS No. 1558-23-2
Cat. No. CS-0512987
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₆N₄
Molecular Weight 110.12
Synonym(s) 1,2,4,5-Tetrazine, 3,6-dimethyl-
SMILES CC1=NN=C(C)N=N1

Description

3,6-Dimethyl-1,2,4,5-tetrazine is a bench-stable, electron-deficient heterocycle that serves as a potent dienophile in inverse electron-demand Diels-Alder reactions. The methyl substituents enhance solubility and reactivity while stabilizing the core against decomposition. This tetrazine integrates readily into bioorthogonal labeling strategies and enables rapid, selective conjugation under physiological conditions.

Application

3,6-Dimethyl-1,2,4,5-tetrazine serves as a versatile dienophile in inverse electron-demand Diels-Alder reactions, enabling rapid access to functionalized heterocycles under mild conditions. Its enhanced stability and crystalline form facilitate handling and purification, while the methyl groups provide favorable electronic tuning for selective cycloadditions. Widely used in bioconjugation and pharmaceutical scaffold construction, it functions reliably in diverse synthetic workflows requiring high reactivity and orthogonality.

Synthesis

Route1
- 37454-64-1
- ~%
- In-stock
  
  1558-23-2
References
- Versteegen, Ron M.; Rossin, Raffaella; Ten Hoeve, Wolter; Janssen, Henk M.; Robillard, Marc S. Angewandte Chemie - International Edition, 2013 , vol. 52, # 52 p. 14112 - 14116 Angew. Chem., 2013 , vol. 125, # 52 p. 14362 - 14366,5
Route2
- 5309-93-3
- ~28%
- In-stock
  
  1558-23-2
References
- Santus, Maria Acta Poloniae Pharmaceutica, 1993 , vol. 50, # 2.3 p. 183 - 188

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 51.56
LogP -0.11656
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Key Words

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3,6-Dimethyl-1,2,4,5-tetrazine

CAS No. 1558-23-2

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