20434-86-0

Basic information

• Product Name: 3,6-Diphenyl-1,4,2,5-dioxadiazine
• Synonyms: 3,6-Diphenyl-1,4,2,5-dioxadiazine
• CAS NO: 20434-86-0
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.24
• Mol File: 20434-86-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-Diphenyl-1,4,2,5-dioxadiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Diphenyl-1,4,2,5-dioxadiazine(20434-86-0)
• EPA Substance Registry System: 3,6-Diphenyl-1,4,2,5-dioxadiazine(20434-86-0)

Safety Data

• Hazardous Substances Data: 20434-86-0(Hazardous Substances Data)

Upstream product

• 873-67-6 benzonitrile oxide 
• 110-86-1 pyridine 
• 698-16-8 benzohydroximoyl chloride 
• 109-06-8 α-picoline 
• 108-89-4 picoline 
• 108-99-6 3-Methylpyridine 
• 59576-20-4 1-phenyl-2-(4-pyridyl)ethanone oxime 
• 670-95-1 4-Phenylimidazole 
• 116273-92-8 methyl (E)-4,4-dimethoxy-3-(pyrrolidin-1-yl)but-2-enoate 
• 934-16-7 phenylhydroxamoyl chloride 
• 59938-06-6 (E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one 

Relevant articles and documents

Studies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silage

During studies directed towards the discovery of nitrile hydrolysing enzymes from thermophiles, vanillin aldoxime was incubated with the thermophilic organism, Geobacillus sp. DDS012 isolated from Italian rye grass (Lolium multiflorum) silage. The predominant product was a dihydro-dimer, which could only be characterised by LC-MS. This was initially imagined to be the product of cycloaddition of vanillin aldoxime with the corresponding nitrile oxide, but preparation of the supposed adduct and model studies excluded this possibility. The rate constant for the second order dimerisation of 4-O-acetyl vanillin nitrile oxide was measured (1.21 × 10-4 M-1 s -1, 0.413 M, 25 °C) and the 13C-NMR signal for the nitrile oxide carbon was observed (δC 34.4, br. t 1J13C,14N circa 50 Hz). Treatment of vanillin aldoxime with potassium persulfate and iron sulfate gave material with the same LC-MS properties as the natural product, which is therefore identified as 5,5′-dehydro-di-(vanillin aldoxime) 1d formed by phenolic oxidative coupling. This journal is The Royal Society of Chemistry.

Study on the 1,3-dipolar cycloaddition reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one with nitrile oxides

1,3-Dipolar cycloaddition (1,3-DC) reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one 1 with nitrile oxides was studied. It was found that besides its C{double bond, long}C participating in the formation of isoxazole rings, trifluoromethyl activated C{dou

SYNTHESIS OF ISOXAZOLES BEARING METHOXYCARBONYL AND FORMYL GROUPS BY 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO OLEFINIC AND ACETYLENIC DIPOLAROPHILES

The 1,3-dipolar cycloaddition of benzo-, bromoformo- and acetonitrile oxides to enamino ester (1) and acetylenic esters (2,3) afforded functionalized isoxazoles in moderate to good yields.Cycloadditions with the enamino ester (1) gave the corresponding me

Reaction of N-Unsubstituted Imidazoles with Benzonitrile Oxide

The behaviour of N-unsubstituted imidazoles 1 with benzonitrile oxide is reported.The results indicate that in solution a ring-chain tautomerism exists between the cycloadduct 3B and the Z-oxime 3A; while in the solid state only the chain form 3A was observed.Oximes of N-benzoylimidazol-2-ones 4, derived from subsequent attack of the 1,3-dipole on both tautomers, and 3,6-diphenyl-1,4,2,5-dioxadiazine 2, an unusual dimer of the benzonitrle oxide, were also isolated.A mechanism involving a zwitterionic intermediate is proposed.The structure of the oximes of N-benzoylimidazol-2-one 4 and 10, derived from benzonitrle oxide and p-toluonitrile oxide respectively, was determined by X-ray diffraction analysis.

ADDITION OF PICOLINES TO BENZONITRILE OXIDE. A DIVERGING PATH WITH 4-PICOLINE

Biscycloadducts are formed by exposing 2- and 3-picoline to benzonitrile oxide. 4-picoline instead affords products of condensation on the methyl group.

CYCLOADDUCTS OF BENZONITRILE OXIDE TO PYRIDINE. A CASE OF A TWO-STEP CYCLOADDITION

Pyridine adds benzonitrile oxide in apolar solvents, affording fair yields of bisadducts III and IV.Quinoline and isoquinoline afford isolable monocycloadducts VIII and IX.