139995-93-0

Basic information

• Product Name: 2-PHENOXYBENZENECARBALDEHYDE OXIME
• Synonyms: 2-PHENOXYBENZENECARBALDEHYDE OXIME;(E)-N-[(2-phenoxyphenyl)methylidene]hydroxylamine
• CAS NO: 139995-93-0
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.23
• Mol File: 139995-93-0.mol

Chemical Properties

• Melting Point: 87-89°C
• Appearance: /
• CAS DataBase Reference: 2-PHENOXYBENZENECARBALDEHYDE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENOXYBENZENECARBALDEHYDE OXIME(139995-93-0)
• EPA Substance Registry System: 2-PHENOXYBENZENECARBALDEHYDE OXIME(139995-93-0)

Safety Data

• Hazardous Substances Data: 139995-93-0(Hazardous Substances Data)

Upstream product

• 19434-34-5 2-(phenoxy)benzaldehyde 
• 108-95-2 phenol 
• 446-52-6 2-Fluorobenzaldehyde 
• 209412-67-9 [1-(2-Phenoxy-phenyl)-meth-(E)-ylideneaminooxy]-ethaneperoxoic acid tert-butyl ester 

Relevant articles and documents

Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes

An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally 1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.

Intramolecular 1,3-dipolar cycloaddition of nitrile N-oxide accompanied by dearomatization

Intramolecular 1,3-dipolar cycloaddition of 2-phenoxybenzonitrile N-oxides to benzene rings, accompanied by dearomatization, formed the corresponding isoxazolines in high yields. The X-ray single-crystal structure analysis revealed that the reaction formed the cis-adduct as a single isomer. The substituents on the benzene rings markedly affected the reaction rate, yield, and structure of the final product.

Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates

Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.

Process for producing alkoxyiminoacetamide compounds and intermediates

A compound of the formula [I] STR1 wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; R is lower alkyl; and ? is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula STR2 wherein X and ?

Process for producing methoxyiminoacetamide compounds and intermediates

A compound of the formula [I]: STR1 wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula [II] STR2 wherein X and are as defined above

Process for producing methoxyiminoacetamide compounds and intermediates

A compound of the formula [I]: STR1 wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; ?is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula [II] STR2 wherein X and ?are as defined abo