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

Base Information

• Chemical Name: 1,2,3-Benzotriazin-4(3H)-one
• CAS No.: 90-16-4
• Molecular Formula: C7H5N3O
• Molecular Weight: 147.136
• Hs Code.: 2933698090
• Mol file: 90-16-4.mol

Synonyms:3,4-Dihydro-4-oxo-1,2,3-benzotriazine;4-Ketobenz-1,2,3-triazine;Benzazimide;Benzazimidone;NSC 13563;NSC 20121;1,2,3-Benzotriazin-4(1H)-one(7CI,9CI);

Chemical Property of 1,2,3-Benzotriazin-4(3H)-one

Chemical Property:

• Appearance/Colour: Buff Colored Powder
• Vapor Pressure: 0.00337mmHg at 25°C
• Melting Point: 216-218 °C(lit.)
• Refractive Index: 1.73
• Boiling Point: 282.4 °C at 760 mmHg
• PKA: -4.67±0.20(Predicted)
• Flash Point: 124.6 °C
• PSA: 58.64000
• Density: 1.47 g/cm³
• LogP: 0.31810
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in most organic solvents.

Purity/Quality:

97% ^*data from raw suppliers

1,2,3-Benzotriazin-4(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 1,2,3-Benzotriazin-4(3H)-one serves as a key precursor in nickel-catalyzed denitrogenative annulation reactions, enabling the synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones through the formation of a reactive five-membered azanickelacycle intermediate. This transformation highlights its utility as a versatile synthon for constructing biologically relevant heterocycles.

Technology Process of 1,2,3-Benzotriazin-4(3H)-one

There total 24 articles about 1,2,3-Benzotriazin-4(3H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

anthranilic acid amide (28144-70-9,88-68-6) → 1,2,3-benzotriazin-4(3H)-one (90-16-4)

Guidance literature:

anthranilic acid amide; With hydrogenchloride; at 0 ℃; for 0.333333h;

With sodium nitrite; In water; at 0 ℃; for 1.66667h;

With ammonium hydroxide; In water; for 0.5h;

DOI:10.1016/j.bmcl.2016.12.065

Reference yield: 82.0%

3-(2-phenylpropan-2-yl)benzo[d][1,2,3]triazin-4(3H)-one → 1,2,3-benzotriazin-4(3H)-one (90-16-4)

Guidance literature:

With trifluoroacetic acid; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.0c00397

Reference yield: 68.0%

3-aminoindazole (874-05-5) → 1,2,3-benzotriazin-4(3H)-one (90-16-4)

Guidance literature:

With ammonium cerium (IV) nitrate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In water; acetonitrile; at 20 ℃; for 16h; Reagent/catalyst; Solvent; Sealed tube;

DOI:10.1021/acs.orglett.8b02813

upstream raw materials:

N-carbamoyl-anthranilic acid amide

3-aminoindazole

anthranilic acid amide

anthranilic acid hydrazide

Downstream raw materials:

3-(hydroxymethyl)benzotriazin-4(3H)-one

3-{3-[4-(4-Methoxy-phenyl)-piperazin-1-yl]-propyl}-3H-benzo[d][1,2,3]triazin-4-one

3-[3-(4-Phenyl-piperidin-1-yl)-propyl]-3H-benzo[d][1,2,3]triazin-4-one

3-[3-(4-Phenyl-piperazin-1-yl)-propyl]-3H-benzo[d][1,2,3]triazin-4-one

Refernces

Nickel-catalyzed denitrogenative annulation reactions of 1,2,3-Benzotriazin-4(3 H)-ones with 1,3-dienes and alkenes

10.1021/jo1008756

The research focuses on nickel-catalyzed denitrogenative annulation reactions of 1,2,3-benzotriazin-4(3H)-ones with 1,3-dienes and alkenes, aiming to provide a synthetic route to substituted 3,4-dihydroisoquinolin-1(2H)-ones, which are found in a variety of plant alkaloids and bioactive compounds. The study demonstrates that a five-membered ring azanickelacycle, generated from 1,2,3-benzotriazin-4(3H)-ones with the release of dinitrogen, can successfully incorporate 1,3-dienes and alkenes, acting as a versatile synthetic intermediate.