165554-70-1

Basic information

• Product Name: 6H-1,2-Oxazine,6-ethoxy-3-phenyl-(9CI)
• Synonyms: 6H-1,2-Oxazine,6-ethoxy-3-phenyl-(9CI)
• CAS NO: 165554-70-1
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.23712
• Product Categories: ETHOXY
• Mol File: 165554-70-1.mol

Chemical Properties

• Boiling Point: 300.8±52.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 6H-1,2-Oxazine,6-ethoxy-3-phenyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-1,2-Oxazine,6-ethoxy-3-phenyl-(9CI)(165554-70-1)
• EPA Substance Registry System: 6H-1,2-Oxazine,6-ethoxy-3-phenyl-(9CI)(165554-70-1)

Safety Data

• Hazardous Substances Data: 165554-70-1(Hazardous Substances Data)

Upstream product

• 40814-66-2 (Z)-2-chloro-1-phenylethan-1-one oxime 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 162191-95-9 2-Methyl-6-phenyl-pyridine-3-carbaldehyde 
• 3558-69-8 2,6-diphenylpyridine 
• 37786-68-8 2,3,6-triphenylpyridine 
• 60272-71-1 2-Butyl-6-phenyl-pyridin 

Relevant articles and documents

Synthesis of 6-ethoxy-6H-1,2-oxazines by hetero Diels-Alder reaction of 1-bromo-2-ethoxyethene with α-nitroso alkenes

A variety of 6H-1,2-oxazines 10 could efficiently be prepared by hetero Diels-Alder reaction of α-nitroso alkenes 2 with 1-bromo-2-ethoxyethene (8) and consecutive elimination of HBr by DBU. Heterodienes 2 were generated in situ from α-halogen oximes 6. Primary cycloadducts 9 were isolated in singular cases, however, an attempt to substitute bromide in 9e by an azido group gave the desired compound 11 only as minor component together with elimation product 10e. 6H-1,2-oxazines 10 are valuable precursors for addition reactions which open new synthetic possibilities.

Hetero Diels-Alder reactions of 2-chloro-1-nitroso-1-phenylethene: Preparation of novel 4-chloro-substituted 1,2-oxazines and subsequent reactions

The cycloaddition of 2-chloro-1-nitroso-1-phenylethene (3), generated in situ from 2,2-dichloro-1-phenylethan-1-one oxime (2) to electron-rich olefins, e.g. silyl enol ethers or alkyl enol ethers, furnished the 4-chloro-substituted 5,6-dihydro-4H-1,2-oxazines and 6H-1,2-oxazines in moderate to good yields and with good diastereoselectivitics. Bromo enol either 18 led to the unexpected α,α-dichloro oxime derivative 21 as well as the halogenated 6H-1,2-oxazines 19 and 20. Starting from 4-chloro-1,2-oxazines 5 and 17, 4-azido-, 4-amino-, 4-hydroxy-, and 4-oxo-substituted 1,2-oxazines were prepared. Hydrogenolysis of 5,6-dihydro-4H-1,2-oxazine 5 afforded amine 31.