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

Base Information

• Chemical Name: 2H-1,4-Benzoxazin-3(4H)-one
• CAS No.: 5466-88-6
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 29349990
• European Community (EC) Number: 628-721-1
• NSC Number: 26354
• UNII: Q0QAF5G662
• DSSTox Substance ID: DTXSID80203118
• Nikkaji Number: J81.041J
• Wikidata: Q72440127
• Metabolomics Workbench ID: 135893
• ChEMBL ID: CHEMBL460153
• Mol file: 5466-88-6.mol

Synonyms:2H-1,4-benzoxazin-3(4H)-one;2H-1,4-benzoxazin-3-one;2H-benzo(b)(1,4)oxazin-3(4H)-one;4H-1,4-benzoxazin-3-one

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

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 172-176 °C
• Refractive Index: 1.563
• Boiling Point: 337.728 °C at 760 mmHg
• PKA: 12.89±0.20(Predicted)
• Flash Point: 158.052 °C
• PSA: 38.33000
• Density: 1.245 g/cm³
• LogP: 1.15550
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: methanol: soluble25mg/mL, clear, colorless
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

2H-1,4-Benzoxazin-3-one ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(=O)NC2=CC=CC=C2O1
• Uses: 2H-1,4-Benzoxazin-3-one is used to prepare benzoxazinone/benzothiazinone analogs of fluconazole with antifungal and anti-Candida activities. It is used to synthesize 1,?4-?benzoxazine derivatives with vasorelaxant activities.

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

There total 55 articles about 2H-1,4-Benzoxazin-3(4H)-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: 99.0%

(2-chloro-phenoxy)-acetic acid amide (35368-68-4) → 3,4-dihydro-3-oxo-2H-1,4-benzoxazine (5466-88-6)

Guidance literature:

With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; at 110 ℃; for 2h; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1039/c7ra09160e

Reference yield: 97.6%

glycolamide (598-42-5) + 1,2-dichloro-benzene (95-50-1) → 3,4-dihydro-3-oxo-2H-1,4-benzoxazine (5466-88-6)

Guidance literature:

With copper acetylacetonate; sodium hydroxide; N,N`-dimethylethylenediamine; In dichloromethane; N,N-dimethyl-formamide; at 60 ℃; for 5h; Reagent/catalyst;

Reference yield: 95.0%

2-Iodophenol (533-58-4) + Chloroacetamide (79-07-2) → 3,4-dihydro-3-oxo-2H-1,4-benzoxazine (5466-88-6)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In 1,4-dioxane; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1039/b906210f

upstream raw materials:

N-(2-hydroxyphenyl)-2-chloroacetamide

2-nitrophenoxyacetic acid

2-chloro-N-(2-methoxyphenyl)acetamide

2-acetamidophenoxyacetic acid

Downstream raw materials:

2-(4-chloro-benzylidene)-4H-benzo[1,4]oxazin-3-one

2-(2-chloro-benzylidene)-4H-benzo[1,4]oxazin-3-one

6-acetyl-4H-benzo[1,4]oxazin-3-one

3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanenitrile

Refernces

• 1、 Ho, Tsai-En,Hsieh, Meng-Jun,Lee, Hon Man,Lee, Jhen-Yi,Wu, Bo-Hsin. "Nickel(ii) complexes containing tridentate ONCi ligands (i = abnormal N-heterocyclic carbene donors) and their catalytic application in Suzuki-Miyaura coupling reaction". . p. 6663 - 6672. Retrieved 2022/05/11.
• 2、 Benarjee,Saritha,Sailaja. "Design and Synthesis of Some New 1,4-Benzoxazine-Isoxazole Hybrids as In Vitro Anticancer Agents". . p. 1783 - 1788. Retrieved 2021/11/04.