2166-14-5

Basic information

• Product Name: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate
• Synonyms: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate;Nsc174664;1,2,4,5-Tetrazine-3,6-dicarboxylic acid, diMethyl ester
• CAS NO: 2166-14-5
• Molecular Formula: C₆H₆N₄O₄
• Molecular Weight: 198.14
• Mol File: 2166-14-5.mol

Chemical Properties

• Melting Point: 176 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 358.9°Cat760mmHg
• Flash Point: 170.9°C
• Appearance: /
• Density: 1.434g/cm³
• Vapor Pressure: 2.47E-05mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: -20°C
• PKA: -3.68±0.10(Predicted)
• CAS DataBase Reference: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate(2166-14-5)
• EPA Substance Registry System: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate(2166-14-5)

Safety Data

• Hazardous Substances Data: 2166-14-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate is used as a synthetic intermediate for the preparation of N-?substituted dibenzoazepine-?pyridazine derivatives. These derivatives are of interest due to their potential as neurologically active drugs, which can be used for the treatment of various neurological disorders.
Used in Organic Synthesis:
Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate is used as a reactant in the Diels-Alder reaction with dibenzoazepines. This reaction allows for the formation of complex molecular structures that can be further modified and utilized in the development of new pharmaceutical compounds.

InChI:InChI=1/C6H6N4O4/c1-13-5(11)3-7-9-4(10-8-3)6(12)14-2/h1-2H3

Upstream product

• 3787-10-8 1,4-Dihydro-1,2,4,5-tetrazin-3,6-dicarbonsaeuredimethylester 
• 67-56-1 methanol 
• 117943-07-4 1,2,4,5-tetrazine-3,6-dicarboxylic acid 

Downstream Products

• 109906-82-3 dimethyl 5H-pyridazino<4,5-b>indole-1,4-dicarboxylate 
• 109906-83-4 5-Benzoyl-5H-pyridazino[4,5-b]indole-1,4-dicarboxylic acid dimethyl ester 
• 2166-27-0 4-phenyl-pyridazine-3,6-dicarboxylic acid dimethyl ester 
• 92144-07-5 dimethyl 4-methoxy-1,2-diazine-3,6-dicarboxylate 
• 81303-94-8 4-amino-3,5-bis(methoxycarbonyl)-1H-pyrazole 
• 112394-07-7 4-Amino-1-(2-methyl-benzyl)-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester 
• 112394-05-5 4-Amino-1-(4-methyl-benzyl)-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester 
• 112394-08-8 4-Amino-1-benzyl-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester 
• 92144-09-7 dimethyl 5-acetyl-4-methoxy-1,2-diazine-3,6-dicarboxylate 
• 23900-51-8 dimethyl 5-phenyl-1,2,4-triazine-3,6-dicarboxylate 
• 150713-77-2 5,5'-dimethoxy-3,3',6,6'-tetrakis(methoxycarbonyl)-4,4'-bi-1,2-diazine 
• 79812-28-5 dimethyl 4-(1-cyclohexen-1-yl)-5-(trimethylsilyl)-3,6-pyridazinedicarboxylate 
• 79812-24-1 4-Benzoyl-5-(trimethylsilyl)-3,6-pyridazindicarbonsaeure-dimethylester 
• 92144-08-6 4-(benzyloxy)-3,6-dicarbomethoxy-1,2-diazine 

Relevant articles and documents

Synthesis of esters and amides of 1,4-dihydro-1,2,4,5-tetrazine-3,6- dicarboxylic acid

Alkyl esters and alkyl amides of 1,4-dihydro-1,2,4,5-tetrazine-3,6- dicarboxylic acid were synthesised and characterised by IR, 1H NMR, EI-MS and elemental analysis. The structure of 1,4-dihydro-1,2,4,5-tetrazine-3, 6-dicarboxylic was confirmed by X-ray diffraction analysis. Some selected compounds were evaluated against P-388 and A-549 cancer cell lines, but showed poor inhibitory activities.

Microwave-promoted synthesis of highly luminescent s-tetrazine-1,3,4-oxadiazole and s-tetrazine-1,3,4-thiadiazole hybrids

Two series of new s-tetrazine derivatives containing 1,3,4-oxadiazole and 1,3,4-thiadiazole rings were synthesized from s-tetrazine-3,6-dicarbohydrazide, triethyl orthoesters and aroyl chlorides. Cyclocondensation reactions for both groups of conjugated arrangements proceeded rapidly and efficiently under microwave irradiation. The obtained compounds exhibited luminescence properties and large quantum yield of emitted photons.

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

An additive-free chemoselective ligation of dual clickable building blocks is demonstrated. The challenge of balancing reactivity and stability was achieved by employing a small, electron-deficient tetrazine bearing an azido group and an enol ether functionalized cyclooctyne. The chemoselective sequence of strain-promoted azide-alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels-Alder (IEDDA) reaction is demonstrated with a cholic acid derived triazide as a molecular surface model for layer-by-layer synthesis.

Novel scaffolds for beta-helix mimicry

Functionalized pyridazine derivatives having a low molecular weight and pharmaceutical compositions thereof are useful as alpha-helix mimetics and for treating conditions and/or disorders mediated by alpha-helix-binding receptors and proteins.