5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid

Base Information

• Chemical Name: 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid
• CAS No.: 1225146-53-1
• Molecular Formula: C₁₄H₁₅N₅O₃
• Molecular Weight: 301.305
• Mol file: 1225146-53-1.mol

Synonyms:5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid

Chemical Property of 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid

Chemical Property:

• Melting Point: 163-170°C (decomposition)

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-[4-(1,2,4,5-Tetrazin-3-yl)benzylamino]-5-oxopentanoic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Acid functionalized tetrazine for inverse electron demand Diels-Alder cycloaddition reactions. The tetrazine will react with strained alkenes such as transcyclooctene, norbornene and cyclopropene to yield a stable covalent linkage. Tetrazines have proven useful in bioorthogonal reactions for many biological imaging and bioconjugation applications.

Technology Process of 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid

There total 8 articles about 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid 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%

glutaric anhydride, (108-55-4) + (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride (1092689-33-2) → 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid (1225146-53-1)

Guidance literature:

In dichloromethane; at 50 ℃;

DOI:10.1021/ja101677r

Reference yield: 76.0%

glutaric anhydride, (108-55-4) + (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetate → 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid (1225146-53-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

Reference yield: 27.0%

5-(4-(cyano)benzylamino)-5-oxopentanoic acid (946852-96-6) + formamidine acetic acid (3473-63-0) → 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid (1225146-53-1)

Guidance literature:

5-(4-(cyano)benzylamino)-5-oxopentanoic acid; formamidine acetic acid; With sulfur; hydrazine; at 25 ℃; for 20h;

With acetic acid;

With sodium nitrite; In water; at 0 ℃;

DOI:10.1016/j.tetlet.2018.06.071

upstream raw materials:

glutaric anhydride,

(4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride

5-(4-(cyano)benzylamino)-5-oxopentanoic acid

formamidine acetic acid

Downstream raw materials:

2,5-dioxopyrrolidin-1-yl 5-((4-(1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanoate

Refernces

• 1、 Zewde, Berhanu,Atoyebi, Olufolasade,Raghavan, Dharmaraj. "An efficient metal catalyst free approach to synthesize 5-(4-(1,2,4,5 tetrazin-3-yl)benzylamino)-5-oxopentanoic acid". . p. 3100 - 3103. Retrieved 2018.
• 2、 Han, Hee-Sun,Devaraj, Neal K.,Lee, Jungmin,Hilderbrand, Scott A.,Weissleder, Ralph,Bawendi, Moungi G.. "Development of a bioorthogonal and highly efficient conjugation method for quantum dots using tetrazine-norbornene cycloaddition". . p. 7838 - 7839. Retrieved 2010.
• 3、 Pahwa, Meenakshi,Jain, Priyanka,Das Saha, Nilanjana,Narayana, Chandrabhas,Agasti, Sarit S.. "Interfacial tetrazine click chemistry mediated assembly of multifunctional colloidosomes". . p. 9534 - 9537. Retrieved 2021/09/28.
• 4、 -. "SPECT imaging agent, labeled precursor and composition thereof and preparation method and application of SPECT imaging agent and labeled precursor of SPECT imaging agent". Paragraph 0023; 0043-0046. . Retrieved 2019/12/08.