2244-91-9

Usage

Chemical class

Tetrazine

Reactivity

Highly reactive

Potential applications

Organic synthesis, materials science, energetic materials, high-energy compounds, photonic materials, and bioconjugation chemistry

Structure

Four nitrogen atoms arranged in a 1,2,4,5-tetrazine ring

Stability

Potentially explosive

Use

Often used as a precursor in the synthesis of energetic materials and high-energy compounds

Versatility

Valuable compound with diverse potential applications

Upstream product

• 87942-21-0 N'-phenylthioformohydrazide 
• 498-66-8 norborn-2-ene 
• 56666-77-4 3-phenyl-5-thioxo-2,5-dihydro-[1,2,3]oxadiazolium betaine 
• 75654-15-8 N,N-Dimethyl-N'-(trimethoxyacetyl)formamidin 
• 100-63-0 phenylhydrazine 
• 123-91-1 1,4-dioxane 
• 78241-07-3 3,6-Diacetyl-1,4-diphenyl-1H,4H-[1,2,4,5]tetrazine 
• 7553-56-2 iodine 
• 622-11-7 α-nitroformaldehyde phenylhydrazone 
• 62-53-3 aniline 
• 59473-82-4 (Z)-α-nitroformaldehyde phenylhydrazone 
• 508191-77-3 3-phenylsydnone 

Downstream Products

• 2209-37-2 2,4-diphenyl-2,4-dihydro-[1,2,4]triazol-3-ylideneamine 
• 622-34-4 1-phenylcyanamide 
• 1885-34-3 N,N'-diphenylformazan 
• 4556-21-2 N-Anilino-N'-phenyl-guanidin 

Relevant academic research and scientific papers

One-Step Conversation of Mesoionic Olate to Thiolate by Lawesson's Reagent

Treatment of mesoionic olates with Lawesson's reagent provides a convenient one-step conversion to mesoionic thiolates.

1,3-Dipolar Cycloadditions, 87. Contributions to the Chemistry of N-Phenylnitrilimine

The N-phenyl derivative 7 is introduced as the first monosubstituted and interceptible nitrilimine whereas the cycloadditions of disubstituted representatives have been preparatively utilized in the past.Photolysis of 2-phenyltetrazole in the presence of methyl acrylate gives rise to methyl 1-phenyl-2-pyrazoline-5-carboxylate which on further irradiation suffers ring cleavage.The sodium salt of α-nitroformaldehyde phenylhydrazone (15) eliminates NaNO2 in refluxing acetonitrile whereby the intermediate 7 is accepted in situ by acrylic ester, styrene and norbornene.The interaction of methyl acrylate with the anionic precursor 15 furnishes further products.The formal dimer of 7, the 1,4-diphenyl-1,4-dihydro-1,2,4,5-tetrazine, is probably formed by reaction of 7 with 15.

Preparation and Reaction of Trimethoxyacetamide and Trimethoxyacetamide Derivates

Trimethoxyacetamide (2a) can be prepared from either trimethoxyacetonitrile (3) or from methyltrimethoxyacetate (1a).Similarly triethoxyacetamide can be obtained from 1b and ammonia.The synthesis of pure 1a is described.Hydrazine hydrate reacts with 1a to form trimethoxyacetohydrazide (6).The compounds 2a and 6 are formylated by tert-butoxy-N,N,N',N'-tetramethylmethanediamine ("aminal ester") at the NH2 group to furnish the formamidine 8 and the formamidrazone 9, respectively. 8 has also been prepared by reaction of N,N-dimethylformamide dimethylacetal with 2a.Reaction of 8 with phenylhydrazine affords the tetrazine 11.CH-acidic compounds such as malonodinitrile and ethyl cyanoacetate are formylated by 8 at the CH2 groups to yield the enamines 12a,b .