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Short Note

2-[6-(2-Hydroxyphenyl)-1,2,4,5-tetrazin-3-yl]phenol

Department of Chemistry, Tamkang University, Taipei 25137, Taiwan
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(4), M339; https://doi.org/10.3390/M339
Submission received: 10 February 2003 / Accepted: 18 June 2003 / Published: 21 June 2003
Molbank 2003 m339 i001
Hydrazine hydrate (99%, 5g, 100 mmol) was added to a solution of 2-cyanophenol (2 g, 16.8 mmol) in absolute ethanol (30 ml) under N2 atmosphere, and the reaction mixture was refluxed for 12 h. During the course of the reaction, the color of the solution changed to yellow, and the yellow precipitate, 2-[6-(2-hydroxyphenyl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl]phenol, produced was readily oxidized in air to 2-[6-(2-hydroxyphenyl)-1,2,4,5- tetrazin-3-yl]phenol (0.9 g, 40% yield ), deep red crystals obtained from recrystallization from tetrahydrofuran.
1H-NMR (300MHz, CDCl3, δppm, JHz): 10.88 (2H, s), 8.66 (2H, d, J=8.1), 7.55 (2H, dd, J=7.2, 5.2), 7.16 (2H, d, J=7.2), 7.13 (2H, dd, J=8.2, 5.2).
IR (KBr, cm-1): 523 (m), 560 (w), 590 (w), 681 (s), 713 (s), 744 (s), 838 (m), 875 (w), 948 (m), 1029 (w), 1050 (m), 1094 (m), 1127 (w), 1155 (m), 1233 (s), 1273 (w), 1331 (w), 1386 (s), 1418 (s), 1472 (m), 1485 (s), 1577 (s), 1616 (s), 3119 (m).
UV-Vis (in CH3CN): 295 (e = 2.14 x 104 mol-1cm-1), 355 (e = 1.86 x 104 mol-1cm-1) and 534 nm (ε = 3.96 x 102 mol-1cm-1).
FAB-MS [M+]: 266.
Calcd: C, 63.15; H, 3.79; N, 21.04 %. Found: C, 63.0; H, 3.8; N, 21.1 %.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgement

Support for this research provided by the National Science Council (Taiwan) is gratefully acknowledged.

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MDPI and ACS Style

Wang, W.-J.; Wang, J.-S. 2-[6-(2-Hydroxyphenyl)-1,2,4,5-tetrazin-3-yl]phenol. Molbank 2003, 2003, M339. https://doi.org/10.3390/M339

AMA Style

Wang W-J, Wang J-S. 2-[6-(2-Hydroxyphenyl)-1,2,4,5-tetrazin-3-yl]phenol. Molbank. 2003; 2003(4):M339. https://doi.org/10.3390/M339

Chicago/Turabian Style

Wang, Wen-Jwu, and Jau-Shuenn Wang. 2003. "2-[6-(2-Hydroxyphenyl)-1,2,4,5-tetrazin-3-yl]phenol" Molbank 2003, no. 4: M339. https://doi.org/10.3390/M339

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