2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid

Base Information

• Chemical Name: 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid
• CAS No.: 1380500-92-4
• Molecular Formula: C₁₀H₈N₄O₂
• Molecular Weight: 216.199

Synonyms:2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid

Chemical Property of 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid

Chemical Property:

• Boiling Point: 477.1±47.0 °C(Predicted)
• Density: 1.394±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

Tetrazine-Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Tetrazine-Acid was found the fastest kinetics for bioorthogonal reaction with trans-cyclooctene (TCO) as the dienophile. The chemical stability of tetrazines is lower compared to methyltetrazines, but it is in acceptable range and thus can be applied for many applications.
• Uses: Tetrazine-acid demonstrates exceptionally fast cycloaddition kinetics with trans-cyclooctene (TCO) as the dienophile (up to 30,000 M-1 s-1). These have been the fastest kinetics reported for a bio orthogonal reaction. The chemical stability of tetrazines is substantially lower compared to methyltetrazines, thus requiring more careful selection of reagents and conditions for chemical transformation. However, tetrazine chemistry is still in an acceptable range for many applications.

Technology Process of 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid

There total 4 articles about 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic 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: 74.0%

4-cyanophenylacetic acid (5462-71-5) + formamidine acetic acid (3473-63-0) → 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid (1380500-92-4)

Guidance literature:

4-cyanophenylacetic acid; formamidine acetic acid; With nickel(II) triflate; hydrazine; at 30 ℃; for 24h; Microwave irradiation;

With hydrogenchloride; sodium nitrite; In water; at 20 ℃; pH=3;

DOI:10.1002/anie.201201117

Reference yield: 74.0%

→ 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid (1380500-92-4)

Guidance literature:

With nickel(II) triflate; hydrazine; at 30 ℃; for 24h; Microwave irradiation; Sealed tube;

With hydrogenchloride; sodium nitrite; In water; pH=3;

Reference yield: 72.0%

dichloromethane (75-09-2) + 4-cyanophenylacetic acid (5462-71-5) → 2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid (1380500-92-4)

Guidance literature:

dichloromethane; 4-cyanophenylacetic acid; With sulfur; hydrazine hydrate; In ethanol; at 50 ℃; for 24h; Microwave irradiation; Sealed tube;

With acetic acid; sodium nitrite; In ethanol; water; Temperature; Sealed tube;

DOI:10.1002/anie.201804878

upstream raw materials:

4-cyanophenylacetic acid

formamidine acetic acid

dichloromethane

Downstream raw materials:

3-(4-phenylacetic acid)-1,2,4,5-tetrazine succinimidyl ester

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