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
• Article Data: 6

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

Description

Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate is an organic compound with the chemical formula C6H6N4O4. It is characterized by the presence of a tetrazine ring fused with two carboxylate groups and two methyl groups. dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate is known for its chemical reactivity and potential applications in various fields.

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

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

Downstream Products

• 56276-33-6 9-phenyl-2-thia-6,7-diaza-spiro[3.5]nona-5,8-diene-5,8-dicarboxylic acid dimethyl ester 
• 82488-95-7 3,6-Dicarbomethoxy-4-<1-(o-aminophenyl)-1-methyl-ethyl>-pyridazin 
• 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 

Relevant articles and documents

A Detailed, Convenient Preparation of Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate

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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.

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.