90-16-4

Basic information

• Product Name: 1,2,3-BENZOTRIAZIN-4(3H)-ONE
• Synonyms: 1,2,3-benzotriazin-4-(1h)-one;1,2,3-benzotriazin-4(1h)-one;1,2,3-Benzotriazin-4-ol;1,2,3-benzotriazin-4-one;3H-1,2,3-Benzotriazin-4-one;4-keto-(3h)-1,2,3-benzotriazine;4-Ketobenz-1,2,3-triazine;4-Ketobenzotriazene
• CAS NO: 90-16-4
• Molecular Formula: C7H5N3O
• Molecular Weight: 147.13
• EINECS: 201-971-5
• Product Categories: pharmacetical;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Triazines
• Mol File: 90-16-4.mol

Chemical Properties

• Melting Point: 216-218 °C(lit.)
• Boiling Point: 282℃
• Flash Point: 125℃
• Appearance: /
• Density: 1.47
• Vapor Pressure: 0.00337mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in most organic solvents.
• PKA: -4.67±0.20(Predicted)
• BRN: 124996
• CAS DataBase Reference: 1,2,3-BENZOTRIAZIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-BENZOTRIAZIN-4(3H)-ONE(90-16-4)
• EPA Substance Registry System: 1,2,3-BENZOTRIAZIN-4(3H)-ONE(90-16-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DM0800000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 90-16-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3-Benzotriazin-4(3H)-one is used as a key intermediate in the synthesis of various organic compounds. It is particularly used to prepare 3-methoxymethyl-3H-benzo[d][1,2,3]triazin-4-one by reacting with dimethoxymethane. 1,2,3-Benzotriazin-4(3H)-one further undergoes thermal condensation with α-amino acids to give 3H-1,4-benzodiazepin-(1H,4H)-2,5-diones.
Used in Pharmaceutical Industry:
1,2,3-Benzotriazin-4(3H)-one is employed as a reagent to synthesize 1,2,3-Benzotriazin-4-one-arylpiperazine derivatives, which are compounds that act as Serotonin (HCl: S274980) receptor ligands. These derivatives have potential applications in the development of drugs targeting the Serotonin receptor.
Used in Antimicrobial Applications:
1,2,3-Benzotriazin-4(3H)-one is part of a group of compounds that exhibit antimicrobial activity. Its ability to inhibit the growth of microorganisms makes it a valuable component in the development of antimicrobial agents and treatments.

Safety Profile

Poison by intraperitoneal route.Experimental reproductive effects. When heated todecomposition it emits toxic fumes of NOx.

InChI:InChI=1/C7H5N3O/c11-7-5-3-1-2-4-6(5)8-10-9-7/h1-4H,(H,8,9,11)

Upstream product

• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 30932-74-2 N-carbamoyl-anthranilic acid amide 
• 28144-70-9 anthranilic acid amide 
• 100-63-0 phenylhydrazine 
• 82573-53-3 N-(1-methyl-1-phenylethyl)benzamide 
• 118-92-3 anthranilic acid 
• 134-20-3 2-carbomethoxyaniline 
• 118-48-9 isatoic anhydride 
• 64908-55-0 3-methoxybenzo[d][1,2,3]triazin-4(3H)-one 
• 2642-71-9 azinphos-ethyl 
• 41225-81-4 3-amino-1,2,3-benzotriazin-4(3H)-one 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 2536-88-1 3H-benzo[1,2,3]triazine-4-thione 

Downstream Products

• 24310-41-6 3-chloromethyl-1,2,3-benzotriazin-4(3H)-one 
• 15561-72-5 3-benzylbenzo[d][1,2,3]triazin-4(3H)-one 
• 64302-63-2 3-(4-methoxy-benzyl)-3H-benzo[d][1,2,3]triazin-4-one 
• 69-72-7 salicylic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 427895-03-2 tert-butyl-2-[2-(4-oxo-4H-benzo[d][1,2,3]-triazin-3-ylethyl)]-3-(4-bromo-phenylthio)propionate 
• 139123-81-2 2-N-(N',N'-diphenylcarbamoyl)triazene benzamide 

Relevant articles and documents

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

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

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.

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

Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, A2 and A3 showed an excellent nematicidal activity with the inhibition rate of 50.4percent and 53.1percent at the concentration of 1.0 mg/L, respectively. The influence of substituent type and position was investigated. The relationship between structure and activity was also preliminary analyzed.

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

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

Herein we report a redox cyclization of amides and sulfonamides with nitrous oxide (N2O) for the direct synthesis of heterocycles. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate could be trapped by N2O gas to achieve redox cyclization. N2O serves as a N-atom donor to mediate the intramolecular coupling of lithium species toward heterocycle formation with free external oxidant. This protocol offers a direct synthesis of heterocycles with features of readily available starting materials, simple operation, and a broad substrate scope.

A benzene and three qinqin alkone of 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof

The invention discloses a 1,4-pentadiene-3-ketone derivative containing benzotriazinone. The 1,4-pentadiene-3-ketone derivative containing benzotriazinone is characterized by having the general formula as shown in the specification, wherein R1 is phenyl, substituted phenyl (p-fluorophenyl, p-chlorophenyl, o-chlorophenyl, 2-methyoxyphenyl, 4-methyoxyphenyl, 4-methylphenyl, 2,4-dimethyoxyphenyl, 3,4-dimethyoxyphenyl, cinnamaldehyde group, 3-nitrophenyl, 2-chloro-5-nitrophenyl and the like), heterocyclic group (furyl, thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrryl and the like) or substituted aromatic heterocyclic group (5-methyl thiazole, 5-methyl-2-thienyl, 4-bromo-2-thienyl and the like), and R2 is a hydrogen atom, methyl (ethyl), methoxyl (ethyoxyl) and the like. The compound disclosedby the invention has relatively high inhibiting activity for citrus canker bacteria, ralstonia solanacearum and tobacco mosaic viruses so as to be used for preparing an agricultural bactericide and anantiviral agent.

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

To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.

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

An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.

Nitrogenous heterocyclic compound with nematocidal activity, preparation method and application thereof

The invention relates to a nitrogenous heterocyclic compound with nematocidal activity, a preparation method and application thereof. Specifically, the invention discloses a compound with a formula (I) or an optical isomer, cis-trans isomer or acceptable salt in agricultural pharmacology and a preparation method thereof. The invention further discloses an agricultural composition containing the compound and application thereof. The compound has excellent nematocidal activity.

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

A series of penta-1,4-dien-3-one containing a benzotriazin-4(3H)-one moiety were prepared and evaluated for their antibacterial and antiviral activities. Bioassays indicated that some compounds exhibited good antibacterial and antiviral activities. Among them, the EC50 values of compound 6d against Xanthomonas axonopodis pv. citri and compound 6l against Ralstonia solanacearum were, respectively, 22.45 and 34.77?μg/mL, which were better than that of thiodiazole copper (51.35 and 87.26?μg/mL, respectively). Meanwhile, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). These results indicated that penta-1,4-dien-3-one derivatives containing benzotriazin-4(3H)-one moiety could play significant roles in searching for novel agrochemicals.