dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate

Base Information

• Chemical Name: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate
• CAS No.: 2166-14-5
• Molecular Formula: C6H6 N4 O4
• Molecular Weight: 198.138
• Hs Code.: 2933990090
• European Community (EC) Number: 808-988-2
• NSC Number: 174664
• DSSTox Substance ID: DTXSID80306219
• Nikkaji Number: J617.271G
• Wikidata: Q82053198
• Mol file: 2166-14-5.mol

Synonyms:1,2,4,5-Tetrazine-3,6-dicarboxylicacid, dimethyl ester (9CI); s-Tetrazine-3,6-dicarboxylic acid, dimethyl ester(7CI,8CI); 3,6-Bis(methoxycarbonyl)-1,2,4,5-tetrazine;3,6-Bis(methoxycarbonyl)tetrazine; 3,6-Dicarbomethoxy-1,2,4,5-tetrazine;Bis(methoxycarbonyl)-s-tetrazine; Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate;Dimethyl 3,6-tetrazinedicarboxylate; NSC 174664

Chemical Property of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate

Chemical Property:

• Vapor Pressure: 2.47E-05mmHg at 25°C
• Melting Point: 176 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 358.9°Cat760mmHg
• PKA: -3.68±0.10(Predicted)
• Flash Point: 170.9°C
• PSA: 104.16000
• Density: 1.434g/cm³
• LogP: -1.16020
• Storage Temp.: -20°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 198.03890469
• Heavy Atom Count: 14
• Complexity: 202

Purity/Quality:

97% ^*data from raw suppliers

3,6-dimethyl1,2,4,5-tetrazine-3,6-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NN=C(N=N1)C(=O)OC
• Uses: 3,6-Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate (CAS# 2166-14-5) can be used in the synthesis of N-?substituted dibenzoazepine-?pyridazine derivatives via Diels-Alder reaction of dibenzoazepines with tetrazines for their use as potential neurologically active drugs.

Technology Process of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate

There total 3 articles about dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,4-Dihydro-1,2,4,5-tetrazin-3,6-dicarbonsaeuredimethylester (3787-10-8) → 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester (2166-14-5)

Guidance literature:

With nitrous gases; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jo00225a076

Reference yield: 52.0%

methanol (67-56-1) + 1,2,4,5-tetrazine-3,6-dicarboxylic acid (117943-07-4) → 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester (2166-14-5)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.dyepig.2019.107865

Reference yield:

→ 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester (2166-14-5)

Guidance literature:

upstream raw materials:

1,4-Dihydro-1,2,4,5-tetrazin-3,6-dicarbonsaeuredimethylester

methanol

1,2,4,5-tetrazine-3,6-dicarboxylic acid

Downstream raw materials:

9-phenyl-2-thia-6,7-diaza-spiro[3.5]nona-5,8-diene-5,8-dicarboxylic acid dimethyl ester

3,6-Dicarbomethoxy-4-<1-(o-aminophenyl)-1-methyl-ethyl>-pyridazin

dimethyl 5H-pyridazino<4,5-b>indole-1,4-dicarboxylate

5-Benzoyl-5H-pyridazino[4,5-b]indole-1,4-dicarboxylic acid dimethyl ester

Refernces

Synthesis and chemistry of unusual bicyclic endoperoxides containing the pyridazine ring

10.1021/jo0345300

The study focuses on the synthesis and chemical transformations of unusual bicyclic endoperoxides containing the pyridazine ring, which are significant due to their potential synthetic applications and pharmacological activities, particularly in cardiovascular systems. The researchers utilized various chemicals, including dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate, unsaturated bicyclic endoperoxides, NEt3 (triethylamine), CoTPP (cobalt(II) tetraphenylporphyrin), and thiourea. These chemicals served as reactants, catalysts, and reductants in the synthesis of bicyclic endoperoxides and their subsequent transformations into pyridazine derivatives and other heterocyclic compounds. The study aimed to develop a method for accessing these complex molecules and explore the diverse chemical reactions of the peroxide functional group within them.