(4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine

Base Information

• Chemical Name: (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine
• CAS No.: 1345955-28-3
• Molecular Formula: C₁₀H₁₁N₅
• Molecular Weight: 201.231

Synonyms:

Chemical Property of (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Methyltetrazine-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Methyltetrazine-Amine possesses substantially improved stability compared to Tetrazine-Amine. It enable click chemistry with TCO (trans-cycloctene).
• Uses: Methyltetrazine-amine is one of the reagents used in the in situ activation of a doxorubicin prodrug using imaging-capable nanoparticles.

Technology Process of (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine

There total 7 articles about (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine 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: 99.0%

tert-butyl N-{[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl]methyl}carbamate (1380500-86-6) → (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine (1345955-28-3)

Guidance literature:

With hydrogenchloride; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.0c00583

Reference yield: 27.0%

4-cyanobenzylamine hydrochloride (15996-76-6) + acetonitrile (75-05-8,26809-02-9) → (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine (1345955-28-3)

Guidance literature:

With nickel(II) triflate; hydrazine hydrate; at 60 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201703103

Reference yield:

tert-butyl N-[(4-cyanophenyl)methyl]carbamate (66389-80-8) → (4-(6-methyl-1,2,4,5-tetrazin-3- yl)phenyl)methaneamine (1345955-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine hydrate; nickel(II) triflate / 24 h / 60 °C / Sealed tube; Inert atmosphere

1.2: Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 1 h / Inert atmosphere

With nickel(II) triflate; hydrazine hydrate; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/c4cc03903c

upstream raw materials:

tert-butyl N-[(4-cyanophenyl)methyl]carbamate

tert-butyl N-{[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl]methyl}carbamate

4-cyanobenzylamine hydrochloride

acetonitrile

Downstream raw materials:

4-({[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl]methyl}carbamoyl)butanoic acid

5-[(2,5-dioxopyrrolidin-1-yl)oxy]-N-[4-(6-methyl-1,2,4,5-tetrazin-3-yl)benzyl]-5-oxopentanamide

2,2',2''-(10-(1-carboxy-4-((2-(5-((4-(6-methyl-1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanamido)ethyl)amino)-4-oxobutyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid

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