32278-16-3

Usage

Uses

Used in Polymer Industry:
3-(TERT-BUTYL)-3,4-DIHYDRO-2H-1,4-BENZOXAZINE is used as a monomer in the production of thermosetting polymers, particularly as a component in epoxy resins. Its inclusion in these resins enhances their heat resistance, flame retardancy, and electrical insulation capabilities, which are crucial for applications in adhesives, coatings, and electronic materials.
Used in Biomedical Materials:
3-(TERT-BUTYL)-3,4-DIHYDRO-2H-1,4-BENZOXAZINE is also being studied for its potential use in biomedical materials due to its biocompatibility and resistance to enzyme degradation. This makes it a promising candidate for applications in the medical field where materials need to be both durable and compatible with biological systems.

InChI:InChI=1/C12H17NO/c1-12(2,3)11-8-14-10-7-5-4-6-9(10)13-11/h4-7,11,13H,8H2,1-3H3/t11-/m0/s1

Upstream product

• 3854-52-2 2-(bromomethyl)-3,3-dimethylbut-1-ene 
• 13547-70-1 1-chloro-3,3-dimethyl-butan-2-one 
• 669694-85-3 2-{[2-(tert-butyl)-2-propenyl]oxy}-1-nitrobenzene 
• 88-75-5 2-hydroxynitrobenzene 
• 32278-17-4 3,3-dimethyl-1-(2-nitrophenoxy)-2-butanone 
• 50-00-0 formaldehyd 
• 5469-26-1 1-Bromopinacolon 

Relevant academic research and scientific papers

N-tosyl-(S)-prolyl chloride in kinetic resolution of racemic heterocyclic amines

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.

Dihydrobenzoxazines and Tetrahydroquinoxalines by a Tandem Reduction-Reductive Amination Reaction

A tandem reduction-reductive amination reaction has been applied to the synthesis of 3,4-dihydro-2H-1,4-benzoxazines and 1-acetyl-1,2,3,4-tetrahydroquinoxalines. The nitroketones required for the benzoxazine ring closures were prepared by (A) alkylation of the anion derived from 2-nitrophenol with an allylic halide or (B) nucleophilic aromatic substitution of an allylic alkoxide on 2-fluoro-1-nitrobenzene followed by ozonolysis. Precursors for the quinoxalines were prepared by alkylation of the anion of 2-nitroacetanilide with an allylic halide followed by ozonolysis. Catalytic hydrogenation of the nitroketones using 5% palladium-on-carbon in methanol then gave the target heterocycles by a reduction-reductive amination sequence. The N-methyl derivatives for both ring systems were easily prepared by adding 5-10 equivalents of aqueous formaldehyde prior to the reduction. The dihydrobenzoxazines were isolated in high yield following purification by chromatographic methods; tetrahydroquinoxalines were isolated in a similar manner and possessed differentiated functionality on the two nitrogens.