21801-14-9

Basic information

• Product Name: 1,2,4,5-Tetrazin-3(2H)-one, 6-phenyl-, hydrazone
• CAS NO: 21801-14-9
• Molecular Formula: C8H8N6
• Molecular Weight: 188.192
• Mol File: 21801-14-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2,4,5-Tetrazin-3(2H)-one, 6-phenyl-, hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-Tetrazin-3(2H)-one, 6-phenyl-, hydrazone(21801-14-9)
• EPA Substance Registry System: 1,2,4,5-Tetrazin-3(2H)-one, 6-phenyl-, hydrazone(21801-14-9)

Safety Data

• Hazardous Substances Data: 21801-14-9(Hazardous Substances Data)

Upstream product

• 14418-30-5 6-amino-3-phenyl-1,2,4,5-tetrazine 
• 36022-11-4 3-phenyl-[1,2,4,5]tetrazine 

Downstream Products

• 78113-93-6 6-n-octylamino-3-phenyl-1,2,4,5-tetrazine 
• 35011-53-1 3-bromo-6-phenyl-1,2,4,5-tetrazine 
• 79357-31-6 N-Isopropylidene-N'-(6-phenyl-[1,2,4,5]tetrazin-3-yl)-hydrazine 

Relevant articles and documents

Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazinesviaa Sonogashira-type cross-coupling reaction

1,2,4,5-Tetrazines have become extremely useful tools in chemical biology. However, the synthesis of some challenging substrates such as asymmetrically disubstituted alkyltetrazines is still a limitation for the widespread use of this class of compounds. Herein we describe an efficient route to these compounds based on the Sonogashira coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine and 3-bromo-6-phenyl-1,2,4,5-tetrazine with terminal alkynes. The preparation of the starting reagents has also been optimized. The alkynyl products have been used as intermediates for the synthesis of dialkyl-tetrazines through a sequence of hydrogenation and re-oxidation with unprecedented yields. The synthetic applicability of this new approach is showcased through the preparation of several unnatural amino acids bearing alkynyl- and alkyl-1,2,4,5-tetrazine fragments.

Occurrence of the SN(ANRORC) Mechanism in the Hydrazination of 1,2,4,5-Tetrazines

3-Alkyl(aryl)-1,2,4,5-tetrazines (7) when treated with hydrazine hydrate were found to undergo a Chichibabin hydrazination into 3-alkyl(aryl)-6-hydrazino-1,2,4,5-tetrazines (8) according to an SN(ANRORC) mechanism. 1H and 13C NMR measurements indicate that the first step in this reaction sequence is the formation of a homoaromatic ? adduct anion, due to attack at C6, and that the second step is the formation of an open-chain intermediate.With 15N-labeled hydrazine, part of the label is found in the 1,2,4,5-tetrazine ring of the 6-hydrazino compounds 8*.NMR evidence is obtained which shows that the hydrazino compounds with 15N-label in the ring (8*II) and with the 15N-label in the hydrazino group (8*I) are formed according to the SN(ANRORC) mechanism.Treatment of 6-amino- or 6-halogeno-1,2,4,5-tetrazines with hydrazine leads to introducing of a hydrazino group at position 6.During this hydrazino deamination and hydrazino dehalogenation part of the molecules were found to react according to the SN(ANRORC) mechanism, the other part followed the SN(AE) pathway.