1,2,4-三唑

1,2,4-三唑
	IUPAC名; 1H-1,2,4-Triazole
識別
CAS號	288-88-0
PubChem	9257
ChemSpider	8900
SMILES	N1C=NC=N1;
InChI	1/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5);
InChIKey	NSPMIYGKQJPBQR-UHFFFAOYAZ
ChEBI	46077
性質
化學式	C2H3N3
摩爾質量	69.07 g·mol−1
外觀	白色固體
密度	1.439 g/cm3
熔點	120—121 °C（248—250 °F；393—394 K）
沸點	260 °C（533 K）
溶解性（水）	非常易溶
pKa	10、3
pKb	11、8
相關物質
相關化學品	1,2,3-三唑; 咪唑
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,2,4-三唑（作為配體時簡稱Htrz）是三唑的異構體之一，化學式 C₂H₃N₃，有一個由兩個碳原子和三個氮原子組成的五元環。1,2,4-三唑及其衍生物有多種應用。^[1]

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結構和性質

1,2,4-三唑是一種平面型分子。它的C-N和N-N鍵都在132至136皮米的範圍內，與芳香性一致。^[2]儘管可以設想1,2,4-三唑有兩種互變異構體，但實際上只有一種存在。

1,2,4-三唑是兩性的，在水溶液中可以N-質子化和去質子化。1,2,4-三唑釒翁離子 (C₂N₃H₄⁺) 的 pK_a為2.45，而中性1,2,4-三唑的pK_a 為10.26。^[3]

製備和存在

1,2,4-三唑類可以通過艾因霍恩-布倫納反應或佩利扎里反應製備。沒有取代基的1,2,4-三唑可以由硫代氨基脲（英語：thiosemicarbazide）被甲酸酰化，然後把產物1-甲酰基-3-硫代氨基脲環化成1,2,4-三唑-3(5)-硫醇，最後用硝酸或過氧化氫氧化，產生1,2,4-三唑。^[5]

1,2,4-三唑類化合物在多種藥物中均有使用。^[6]^[7]一些值得注意的三唑類包括抗真菌藥氟康唑和伊曲康唑。^[8]1,2,4-三唑陰離子在配位化學中是一種常見的橋接配體。^[9]

參考資料

[1]
Potts K. T. The Chemistry of 1,2,4-Triazoles.. Chemical Reviews. 1961, 61 (2): 87–127. doi:10.1021/cr60210a001.
[2]
Jeffrey, G. A.; Ruble, J. R.; Yates, J. H. Neutron diffraction at 15 and 120 K and ab initio molecular-orbital studies of the molecular structure of 1,2,4-triazole. Acta Crystallographica Section B Structural Science. 1983, 39 (3): 388–394. doi:10.1107/S010876818300258X.
[3]
Garratt, Peter J. 1,2,4-Triazoles. Comprehensive Heterocyclic Chemistry II. 1996: 127–163. ISBN 9780080965185. doi:10.1016/B978-008096518-5.00080-0.
[4]
Grosjean, Arnaud; Négrier, Philippe; Bordet, Pierre; Etrillard, Céline; Mondieig, Denise; Pechev, Stanislav; Lebraud, Eric; Létard, Jean-François; Guionneau, Philippe. Crystal Structures and Spin Crossover in the Polymeric Material [Fe(HTRZ)2(TRZ)](BF4) Including Coherent-Domain Size Reduction Effects (PDF). European Journal of Inorganic Chemistry. 2013, 2013 (5–6): 796–802 [2021-10-11]. doi:10.1002/ejic.201201121. （原始內容 (PDF)存檔於2021-11-05）.
[5]
C. Ainsworth. 1,2,4-Triazole. Organic Syntheses. 1960, 40: 99. doi:10.15227/orgsyn.040.0099.
[6]
Keri, Rangappa S.; Patil, Siddappa A.; Budagumpi, Srinivasa; Nagaraja, Bhari Mallanna. Triazole: A Promising Antitubercular Agent. Chemical Biology & Drug Design. 2015, 86 (4): 410–423. PMID 25643871. doi:10.1111/cbdd.12527.
[7]
Kaur, Ramandeep; Ranjan Dwivedi, Ashish; Kumar, Bhupinder; Kumar, Vinod. Recent Developments on 1,2,4-Triazole Nucleus in Anticancer Compounds: A Review. Anti-Cancer Agents in Medicinal Chemistry. 2016, 16 (4): 465–489. PMID 26286663. doi:10.2174/1871520615666150819121106.
[8]
Kathiravan, Muthu K.; Salake, Amol B.; Chothe, Aparna S.; Dudhe, Prashik B.; Watode, Rahul P.; Mukta, Maheshwar S.; Gadhwe, Sandeep. The biology and chemistry of antifungal agents: A review. Bioorganic & Medicinal Chemistry. 2012, 20 (19): 5678–5698. PMID 22902032. doi:10.1016/j.bmc.2012.04.045.
[9]
Haasnoot, Jaap G. Mononuclear, oligonuclear and polynuclear metal coordination compounds with 1,2,4-triazole derivatives as ligands. Coordination Chemistry Reviews. 2000,. 200-202: 131–185. doi:10.1016/S0010-8545(00)00266-6.

[1] [1]
Potts K. T. The Chemistry of 1,2,4-Triazoles.. Chemical Reviews. 1961, 61 (2): 87–127. doi:10.1021/cr60210a001.

[2] [2]
Jeffrey, G. A.; Ruble, J. R.; Yates, J. H. Neutron diffraction at 15 and 120 K and ab initio molecular-orbital studies of the molecular structure of 1,2,4-triazole. Acta Crystallographica Section B Structural Science. 1983, 39 (3): 388–394. doi:10.1107/S010876818300258X.

[3] [3]
Garratt, Peter J. 1,2,4-Triazoles. Comprehensive Heterocyclic Chemistry II. 1996: 127–163. ISBN 9780080965185. doi:10.1016/B978-008096518-5.00080-0.

[4] [4]
Grosjean, Arnaud; Négrier, Philippe; Bordet, Pierre; Etrillard, Céline; Mondieig, Denise; Pechev, Stanislav; Lebraud, Eric; Létard, Jean-François; Guionneau, Philippe. Crystal Structures and Spin Crossover in the Polymeric Material [Fe(HTRZ)2(TRZ)](BF4) Including Coherent-Domain Size Reduction Effects (PDF). European Journal of Inorganic Chemistry. 2013, 2013 (5–6): 796–802 [2021-10-11]. doi:10.1002/ejic.201201121. （原始內容 (PDF)存檔於2021-11-05）.

[5] [5]
C. Ainsworth. 1,2,4-Triazole. Organic Syntheses. 1960, 40: 99. doi:10.15227/orgsyn.040.0099.

[6] [6]
Keri, Rangappa S.; Patil, Siddappa A.; Budagumpi, Srinivasa; Nagaraja, Bhari Mallanna. Triazole: A Promising Antitubercular Agent. Chemical Biology & Drug Design. 2015, 86 (4): 410–423. PMID 25643871. doi:10.1111/cbdd.12527.

[7] [7]
Kaur, Ramandeep; Ranjan Dwivedi, Ashish; Kumar, Bhupinder; Kumar, Vinod. Recent Developments on 1,2,4-Triazole Nucleus in Anticancer Compounds: A Review. Anti-Cancer Agents in Medicinal Chemistry. 2016, 16 (4): 465–489. PMID 26286663. doi:10.2174/1871520615666150819121106.

[8] [8]
Kathiravan, Muthu K.; Salake, Amol B.; Chothe, Aparna S.; Dudhe, Prashik B.; Watode, Rahul P.; Mukta, Maheshwar S.; Gadhwe, Sandeep. The biology and chemistry of antifungal agents: A review. Bioorganic & Medicinal Chemistry. 2012, 20 (19): 5678–5698. PMID 22902032. doi:10.1016/j.bmc.2012.04.045.

[9] [9]
Haasnoot, Jaap G. Mononuclear, oligonuclear and polynuclear metal coordination compounds with 1,2,4-triazole derivatives as ligands. Coordination Chemistry Reviews. 2000,. 200-202: 131–185. doi:10.1016/S0010-8545(00)00266-6.

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