Production Method 1

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Solvents: Acetonitrile ;  1 h, rt

Reference

Catalyst-free oxidative N-N coupling for the synthesis of 1,2,3-triazole compounds with tBuONO

Cai, Yue-Ming; Zhang, Xin; An, Cui; Yang, Ye-Fei; Liu, Wei; et al, Organic Chemistry Frontiers, 2019, 6(9), 1481-1484

Production Method 2

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  0 °C; 40 min, 0 °C; 1 h, 0 °C
1.3 Reagents: Ammonia Solvents: Water ;  0 °C; 30 min, pH 7 - 8, 0 °C

Reference

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita

Chang, Yaning; Zhang, Jingwei; Chen, Xiulei; Li, Zhong; Xu, Xiaoyong, Bioorganic & Medicinal Chemistry Letters, 2017, 27(11), 2641-2644

Production Method 3

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  40 min, 0 °C; 2 h, 0 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, 0 °C; 15 min, pH 8

Reference

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

Chen, Xiulei ; Zhou, Zhen; Li, Zhong; Xu, Xiaoyong, Phosphorus, 2020, 195(3), 194-200

Production Method 4

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  20 min, 0 °C
1.2 Solvents: Dimethylformamide ;  40 min, 0 °C; 1 h, 0 °C
1.3 Reagents: Ammonia Solvents: Water ;  pH 10, 0 °C; 15 min, 0 °C
1.4 Reagents: Hydrogen ion ;  30 min, pH 2, 0 °C

Reference

Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

Wang, Gaolei; Chen, Xiulei; Deng, Yayun; Li, Zhong; Xu, Xiaoyong, Journal of Agricultural and Food Chemistry, 2015, 63(31), 6883-6889

Production Method 5

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  1 h, 0 °C; 0 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized, rt

Reference

Synthesis and Biological Activities of Some New Benzotriazinone Derivatives Based on Molecular Docking; Promising HepG2 Liver Carcinoma Inhibitors

El Rayes, Samir M. ; Ali, Ibrahim A. I.; Fathalla, Walid; Mahmoud, Mostafa A. A., ACS Omega, 2020, 5(12), 6781-6791

Production Method 6

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  40 min, 0 °C; 2 h, 0 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, 0 °C; 15 min, 0 °C

Reference

Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita

Chen, Xiulei; Jia, Haowu; Li, Zhong; Xu, Xiaoyong, Chinese Chemical Letters, 2019, 30(6), 1207-1213

Production Method 7

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 °C; 1 h, 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Design, synthesis and nematicidal activities of trifluorobutene hydroxamic acid derivatives against Meloidogyne incognita

Chen, Diancong; Yang, Haiping; Li, Zhong; Maienfisch, Peter; Xu, Xiaoyong, Journal of Molecular Structure, 2022, 1264,

Production Method 8

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  20 min, 0 °C
1.2 Solvents: Dimethylformamide ;  40 min, 0 °C; 1 h, 0 °C
1.3 Reagents: Ammonia Solvents: Water ;  pH 10; 15 min
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 2; 30 min

Reference

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita

Zhang, Ruifeng; Guo, Wei; Wang, Gaolei; Chen, Xiulei; Li, Zhong; et al, Bioorganic & Medicinal Chemistry Letters, 2020, 30(17),

Production Method 9

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid ,  Nitrite (polymer-supported) Solvents: Methanol ;  1 h, 0 °C; 0 °C → rt; 1 h, rt

Reference

One-pot synthesis of N-substituted benzannulated triazoles via stable arene diazonium salts

McGrory, Rochelle; Faggyas, Reka J.; Sutherland, Andrew, Organic & Biomolecular Chemistry, 2021, 19(27), 6127-6140

Production Method 10

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  cooled; 1 h, cooled
1.2 Reagents: Sodium hydroxide ;  pH 7 - 8

Reference

Synthesis, antibacterial, and antiviral activities of novel penta-1,4-dien-3-one derivatives containing a benzotriazin-4(3H)-one moiety

Zhang, Ju-Ping; Li, Qin; Zhang, Cheng; Li, Pu; Chen, Li-Juan; et al, Chemical Papers, 2018, 72(9), 2193-2202

Production Method 11

90-16-4

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ;  0 °C; overnight, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Redox Cyclization of Amides and Sulfonamides with Nitrous Oxide for Direct Synthesis of Heterocycles

Lai, Zhencheng; Wang, Chaorong; Li, Jiaming; Cui, Sunliang, Organic Letters, 2020, 22(5), 2017-2021

Production Method 12

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Dimethylformamide ,  Water ;  40 min, 0 °C; 1 h, 0 - 5 °C
1.2 Reagents: Ammonia Solvents: Water ;  pH 10.0, 0 - 5 °C; 30 min, 0 - 5 °C
1.3 pH 2.0

Reference

Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A4 hydrolase aminopeptidase inhibitors

Zhang, Fan; Wu, Dang; Wang, Gao-Lei; Hou, Shuang; Ping, Ou-Yang; et al, Chinese Chemical Letters, 2017, 28(5), 1044-1048

Production Method 13

88-68-6

90-16-4

Reaction Conditions

1.1 Reagents: Iodine ,  Sodium nitrite Solvents: Acetonitrile ;  rt; 3 h, 80 °C

Reference

NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

Barak, Dinesh S.; Mukhopadhyay, Sushobhan; Dahatonde, Dipak J.; Batra, Sanjay, Tetrahedron Letters, 2019, 60(3), 248-251

Production Method 14

88-68-6

90-16-4

Reaction Conditions

Reference

Preparation of oligonucleotides containing dAICA using an unexpected side-reaction observed on a protected derivative of 2-aza-2'-deoxyinosine

Fernandez-Forner, Dolors; Eritja, Ramon; Bardella, Francesc; Ruiz-Perez, Catalina; Solans, Xavier; et al, Tetrahedron, 1991, 47(42), 8917-30

Production Method 15

874-05-5

90-16-4

Reaction Conditions

1.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin ,  Water ,  Oxygen ,  Ceric ammonium nitrate Solvents: Acetonitrile ;  16 h, rt

Reference

Oxidative Rearrangement of 3-Aminoindazoles for the Construction of 1,2,3-Benzotriazine-4(3H)-ones at Ambient Temperature

Zhou, Yao ; Wang, Ya; Lou, Yixian; Song, Qiuling, Organic Letters, 2018, 20(20), 6494-6497

Production Method 16

88-68-6

90-16-4

Reaction Conditions

Reference

Product subclass 1: 1,2,3-triazines and phosphorus analogues

Doepp, H.; Doepp, D., Science of Synthesis, 2004, 17, 223-355

1,2,3-Benzotriazin-4(3H)-one Raw materials

• 1H-Indazol-3-amine
• 2-Aminobenzamide

1,2,3-Benzotriazin-4(3H)-one Preparation Products

• 1,2,3-Benzotriazin-4(3H)-one (90-16-4)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzo-1,2,3-triazines
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

1,2,3-Benzotriazin-4(3H)-one: A Comprehensive Overview

The compound 1,2,3-Benzotriazin-4(3H)-one (CAS No. 90-16-4) is a heterocyclic aromatic compound with a unique structure that has garnered significant attention in various fields of chemistry and materials science. This compound belongs to the class of benzotriazines, which are derivatives of benzene fused with a triazine ring. The benzotriazinone system is characterized by its three nitrogen atoms in the six-membered ring, making it a versatile platform for chemical modifications and applications.

Recent studies have highlighted the potential of benzotriazinones as building blocks for advanced materials. For instance, researchers have explored the use of 1,2,3-benzotriazin-4(3H)-one in the development of high-performance polymers and organic semiconductors. Its aromaticity and nitrogen-rich structure make it an ideal candidate for applications in optoelectronics and energy storage devices. Moreover, the compound's ability to undergo various substitution reactions has enabled the synthesis of derivatives with tailored properties.

The synthesis of 1,2,3-benzotriazin-4(3H)-one involves a multi-step process that typically starts with the reaction of o-phenylenediamine with an aldehyde or ketone under specific conditions. Recent advancements in catalytic methods have improved the efficiency and selectivity of this synthesis pathway. For example, the use of transition metal catalysts has been shown to significantly reduce reaction times while maintaining high yields.

In terms of chemical properties, benzotriazinones exhibit remarkable thermal stability and resistance to oxidation. These characteristics make them suitable for use in high-temperature applications such as aerospace materials and fire-retardant coatings. Additionally, their electronic properties have been leveraged in the development of organic light-emitting diodes (OLEDs) and photovoltaic cells.

Recent research has also focused on the biological activity of benzotriazinones, particularly their potential as drug candidates. Studies have shown that certain derivatives exhibit anti-inflammatory and anticancer properties. For instance, a derivative of 1,2,3-benzotriazin-4(3H)-one has been found to inhibit specific enzymes involved in inflammatory pathways, making it a promising lead compound for therapeutic development.

The versatility of benzotriazinones extends to their application in catalysis. The nitrogen atoms in the ring can act as Lewis bases or coordinate with metal ions to form complexes with unique catalytic properties. This has led to their use in asymmetric catalysis and organocatalytic reactions.

In conclusion, 1,2,3-benzotriazin-4(3H)-one (CAS No. 90-16-4) is a multifaceted compound with a wide range of applications across various scientific disciplines. Its structural features and reactivity make it an invaluable tool for researchers working in materials science, pharmacology, and catalysis. As ongoing studies continue to uncover new properties and applications, this compound is poised to play an increasingly important role in both academic research and industrial innovation.

• 28230-32-2(HOOBT; 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one)
• 41225-81-4(1,2,3-Benzotriazin-4(3H)-one,3-amino-)
• 59708-31-5(Benzamide, 2-(3-ethyl-3-methyl-1-triazenyl)-)
• 66974-84-3(N-acetylimino-2-[2-(dimethylamino)hydrazinyl]benzamide)
• 36772-63-1(7-chloro-3,4-dihydro-1,2,3-benzotriazin-4-one)
• 33330-89-1( )
• 830321-64-7(1,2,3-Benzotriazin-4(1H)-one, 6,8-dimethyl-)
• 22305-44-8(1,2,3-Benzotriazin-4(3H)-one,3-methyl-)
• 116466-08-1(benzoic acid, 2-(3-butyl-3-methyl-1-triazeno)-, hydrazide)
• 59255-02-6( )