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(4H)-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
• General Description: 2H-1,4-Benzoxazin-3(4H)-one is a heterocyclic compound that can be efficiently synthesized via a mild, chemoselective one-pot reaction using o-aminophenols, the ionic liquid [omim][BF₄], and DBU as a base. This method is notable for its high yields, short reaction times, and the recyclability of the ionic liquid, making it an environmentally friendly approach. The versatility of the reaction allows for the use of diverse substrates, including less reactive ones, highlighting its broad applicability in organic synthesis.

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-benzylidene-4H-benzo[1,4]oxazin-3-one

4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

4-methyl-4H-benzo[1,4]oxazin-3-one

3,4-dihydro-7-chloro-3-oxo-2H-1,4-benzoxazine

Refernces

[Omim][BF₄], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones

10.1016/j.tetlet.2010.01.122

The research presents an efficient one-pot chemoselective synthesis of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives from o-aminophenols using the ionic liquid [omim][BF4] and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature. The ionic liquid [omim][BF4] serves as a green and recyclable medium, allowing for the recovery and reuse of the IL over nine cycles without significant loss of performance. DBU acts as a crucial base in the reaction, facilitating the cyclization process to achieve high yields of the desired products in short reaction times. The procedure is mild, involves a broad range of starting materials, and demonstrates chemoselectivity, making it a significant advancement in the synthesis of benzoxazinones. The study also explores the use of various o-aminophenols and 2-bromoalkanoates, including less reactive substrates, showcasing the versatility and applicability of this method in organic synthesis.