3534-33-6

Upstream product

• 82344-61-4 8-Chloro-3,5-dimethyl-3,4-dihydro-2H-benzo[e][1,3]oxazine 
• 237431-65-1 4-Methyl-2-{[methyl-((R)-1-phenyl-ethyl)-amino]-methyl}-phenol 
• 237431-64-0 6-methyl-3-[(1R)-1-phenylethyl]3,4-dihydro-2H-1,3-benz[e]oxazine 
• 50-00-0 formaldehyd 
• 237431-66-2 2-hydroxy-5-methyl-N-methylbenzylamine 
• 106-44-5 p-cresol 
• 74-89-5 methylamine 

Downstream Products

• 3534-25-6 2-({[(2-hydroxy-5-methylphenyl)methyl](methyl)amino}methyl)-4-methylphenol 
• 7204-35-5 2-(dimethylamino-methyl)-4-methyl-phenol 

Relevant academic research and scientific papers

Crystal structure and novel solid-state fluorescence behavior of the model benzoxazine monomer: 3,4-Dihydro-3,6-dimethyl-1,3,2H-benzoxazine

Solid-state fluorescent behavior of the model benzoxazine monomer, 3,4-dihydro-3,6-dimethyl-1,3,2H-benzoxazine denoted as MM, was firstly reported. Three characteristic fluorescence peaks were observed, i.e., (1) the ultraviolet peak at 317 nm with the excitation wavelength of 258 nm, (2) the blue emission peak at 450 nm with the excitation wavelength of 324 nm and (3) the other blue fluorescent peak at 454 nm with the excitation wavelength of 360 nm. It was proved that the benzoxazine core was responsible for the fluorescence of blue light due to the absence of the emission peak in the ring-opening benzoxazine dimer with the same moieties as the benzoxazine monomer MM. The single crystal X-ray structure of the compound MM recorded at 100 K showed that the irregular chair conformation of the ring-closure benzoxazine MM gave rise to the fluorescent property since all the members of the oxazine ring other than nitrogen atom arranged themselves at the plane of the benzene ring.

Vibrational assignments of 3-alkyl-3,4-dihydro-6-methyl-2H-1,3-benzoxazines in the fingerprint region

Fundamental vibrational assignments of a series of 3-alkyl-3,4-dihydro-6-methyl-2H-1,3-benzoxazines are made by analysis of the fingerprint region (2000-500 cm-1) of their infrared and Raman spectra.The linear amine group is varied from methyl to amyl which alters the position of the peaks resulting from the oxazine ring but has little influence on the benzene ring vibrations.To aid in the peak assignments, 3,4-dideutero-3,6-dimethyl-2D-1,3-benzoxazine has also been synthesized.The structures of the compounds are verified by 1H and 13C NMR.

Polymerization of p-cresol, formaldehyde, and piperazine and structure of monofunctional benzoxazine-derived oligomers

By using a secondary amine, e g. piperazine, a Mannich base polymer, having similar structure to the traditional polybenzoxazine, is synthesized. Unlike all the reported polybenzoxazines that are colored, the white polymer shows good thermal property that is close to the degradation temperature of the polybenzoxazine derived from difunctional benzoxazine monomers. 31P NMR spectroscopy in combination with facile phosphorus derivatization and previous model compound studies are utilized to clarify the structures of piperazine-based systems as well as the main chain and end group of traditional polybenzoxazines.

Self termination of ring opening reaction of p-substituted phenol-based benzoxazines: An obstructive effect via intramolecular hydrogen bond

(Chemical Equation Presented) The ring opening polymerizations of p-substituted phenol-based benzoxazines are self-terminated as soon as dimers form. The polymerization of benzoxazine monomers does not proceed according to the theoretical mechanism even though the conditions, temperature, molar ratio, solvent polarity, and reactant ratio are varied. The speculated mechanism, involving the unique structure of a dimer with interand intramolecular hydrogen bonds, is applied to explain an obstructive effect on ring opening polymerization. In this article, we clarify an important case which the stereo structure of the compound controls the reaction and prevents the polymerization expected from the theoretical mechanism.

Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne - Ketenes

Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)4-catalyzed cross-coupling factions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132°C) promoted a retro-ene reaction to produce enyne - ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in he same molecule simultaneously provided many opportunities for intramolecular decay through disproportionate, radical - radical combination, and the formation of o-quinone methide.

Etude spectroscopique (i.r., RMN1H et 13C) de derives de la N-methyl 2H-dihydro-3,4 benzoxazine-1,3. Influence de la substitution de l'homocycle.

The spectroscopic properties (i.r., NMR1H and 13C) of substituted N-methyl 2H-3,4-dihydro 1,3-benzoxazines has been studied.Infrared and NMR1H data allow to determine structures of isomers and NMR13C exhibits electronic and steric effects of substituents.