58418-25-0

Basic information

• Product Name: 2-(tert-butylamino)-4H-3,1-benzoxazin-4-one
• CAS NO: 58418-25-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.2518
• Mol File: 58418-25-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 327.9°C at 760 mmHg
• Flash Point: 152.1°C
• Density: 1.18g/cm³
• Vapor Pressure: 0.000197mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 2-(tert-butylamino)-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-butylamino)-4H-3,1-benzoxazin-4-one(58418-25-0)
• EPA Substance Registry System: 2-(tert-butylamino)-4H-3,1-benzoxazin-4-one(58418-25-0)

Safety Data

• Hazardous Substances Data: 58418-25-0(Hazardous Substances Data)

Usage

General Description

2-(tert-butylamino)-4H-3,1-benzoxazin-4-one is a chemical compound that belongs to the benzoxazine class. It is a heterocyclic compound containing a benzene ring fused to a oxazine ring, with a tert-butylamino group attached at the 2-position. 2-(tert-butylamino)-4H-3,1-benzoxazin-4-one is used in the synthesis of various pharmaceuticals and organic compounds. It has also been studied for its potential biological activities, including its role as a potential anticancer agent and its antioxidant properties. Additionally, it has been investigated for its potential use in the development of new materials, such as organic light emitting diodes and polymers.

Upstream product

• 5100-23-2 2-isocyanatobenzoyl chloride 
• 75-64-9 tert-butylamine 
• 201230-82-2 carbon monoxide 
• 15054-54-3 1-tert-butyl-3-phenylurea 
• 119072-55-8 tert-butylisonitrile 
• 118-92-3 anthranilic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 31162-13-7 2-azidobenzoic acid 
• 16714-25-3 2-azidobenzaldehyde 
• 54467-95-7 1-azido-2-iodo-benzene 
• 615-43-0 2-iodophenylamine 

Relevant articles and documents

Palladium-catalyzed synthesis of 2-aminobenzoxazinones by aerobic oxidative coupling of anthranilic acids and isocyanides

Isocyanides have emerged as valuable C1 building blocks in palladium catalysis. Their potential has, however, mainly been exploited for the synthesis of amidines and amidine-containing heterocycles. To illustrate the broader applicability of isocyanides, we have recently developed a novel oxidative coupling of diamines and isocyanides furnishing valuable guanidine-containing heterocycles. We here report the extension of this protocol to the coupling of anthranilic acids and isocyanides leading to medicinally relevant 2-aminobenzoxazinones. This is a particularly challenging substrate class for this reaction due to the possibility of undesired decarboxylative pathways and the susceptibility of the products to nucleophilic attack. Therefore, this work underlines the generality and broad potential of the oxidative coupling of bisnucleophiles and isocyanides, facilitating the further implementation of this chemistry in library design.

Synthesis of Diverse Nitrogen Heterocycles via Palladium-Catalyzed Tandem Azide–Isocyanide Cross-Coupling/Cyclization: Mechanistic Insight using Experimental and Theoretical Studies

A rapid and elegant tandem azide–isocyanide cross-coupling/cyclization protocol has been developed based on a nitrene transfer reaction. The palladium-catalyzed ligand-free methodology led to the synthesis of three different heterocyclic scaffolds with excellent atom/step/redox economy. Studies based on first-principles-based quantum calculations and control experiments unraveled a concerted process of nitrene transfer reaction on isocyanides, ruling out the metallaaziridine intermediate reported earlier. This finding could pave the way for novel applications of nitrene transfer reactions to generate bioactive heterocycles. (Figure presented.).

Room-temperature palladium-catalyzed C-H activation: Ortho-carbonylation of aniline derivatives

Pd and CO - ureally got me! The title reaction proceeds efficiently at 18°C under CO (1 atm) with 5 % [Pd(OTs)2 (MeCN)2] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ=benzoquinone, Ts=4-toluenesulfonyl).