Phenylhydroxylamine is the organic compound with the formula C6H5NHOH. It is an intermediate in the redox-related pair C6H5NH2 and C6H5NO. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or O-phenylhydroxylamine.
Like other hydroxylamines it will react with aldehydes to form nitrones, illustrative is the condensation with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipolar compound:[4]
C6H5NHOH + C6H5CHO → C6H5N(O)=CHC6H5 + H2O
Phenylhydroxylamine is attacked by NO+ sources to give cupferron:[5]
^P. W. Oxley, B. M. Adger, M. J. Sasse, M. A. Forth (1989). "N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon". Organic Syntheses. 67: 187. doi:10.15227/orgsyn.067.0187.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl (1966). "2,3,5-Triphenylisoxazolidine". Organic Syntheses. 46: 127. doi:10.15227/orgsyn.046.0127.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^C. S. Marvel (1925). "Cupferron". Organic Syntheses. 4: 19. doi:10.15227/orgsyn.004.0019.
April 11, 2024
phenylhydroxylamine, organic, compound, with, formula, c6h5nhoh, intermediate, redox, related, pair, c6h5nh2, c6h5no, should, confused, with, isomer, phenylhydroxylamine, phenylhydroxylamine, namespreferred, iupac, name, hydroxyanilineother, names, beta, pheny. Phenylhydroxylamine is the organic compound with the formula C6H5NHOH It is an intermediate in the redox related pair C6H5NH2 and C6H5NO Phenylhydroxylamine should not be confused with its isomer a phenylhydroxylamine or O phenylhydroxylamine Phenylhydroxylamine NamesPreferred IUPAC name N HydroxyanilineOther names beta phenylhydroxylamine phenylhydroxylamine N hydroxybenzeneamine hydroxylaminobenzeneIdentifiersCAS Number 100 65 2 Y3D model JSmol Interactive imageChEBI CHEBI 28902 NChemSpider 7237 NECHA InfoCard 100 002 614EC Number 209 711 2KEGG C02720 NPubChem CID 7518UNII 282MU82Z9A NCompTox Dashboard EPA DTXSID3025889InChI InChI 1S C6H7NO c8 7 6 4 2 1 3 5 6 h1 5 7 8H NKey CKRZKMFTZCFYGB UHFFFAOYSA N NInChI 1 C6H7NO c8 7 6 4 2 1 3 5 6 h1 5 7 8HKey CKRZKMFTZCFYGB UHFFFAOYAKSMILES ONC1 CC CC C1PropertiesChemical formula C6H7NOMolar mass 109 1274 g molAppearance yellow needlesMelting point 80 to 81 C 176 to 178 F 353 to 354 K Magnetic susceptibility x 68 2 10 6 cm3 molRelated compoundsRelated compounds hydroxylamine nitrosobenzeneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesPreparation editThis compound can be prepared by the reduction of nitrobenzene with zinc in the presence of NH4Cl 1 2 Alternatively it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H2 source over a rhodium catalyst 3 Reactions edit nbsp Cupferron N nitroso N phenylhydroxylamine a reagent for qualitative inorganic analysis is prepared from phenylhydroxylamine Phenylhydroxylamine is unstable to heating and in the presence of strong acids easily rearranges to 4 aminophenol via the Bamberger rearrangement Oxidation of phenylhydroxylamine with dichromate gives nitrosobenzene Like other hydroxylamines it will react with aldehydes to form nitrones illustrative is the condensation with benzaldehyde to form diphenylnitrone a well known 1 3 dipolar compound 4 C6H5NHOH C6H5CHO C6H5N O CHC6H5 H2OPhenylhydroxylamine is attacked by NO sources to give cupferron 5 C6H5NHOH C4H9ONO NH3 NH4 C6H5N O NO C4H9OHReferences edit E Bamberger Ueber das Phenylhydroxylamin Chemische Berichte volume 27 1548 1557 1894 E Bamberger Ueber die Reduction der Nitroverbindungen Chemische Berichte volume 27 1347 1350 1894 first report O Kamm 1941 Phenylhydroxylamine Organic Syntheses 4 57 doi 10 15227 orgsyn 004 0057 P W Oxley B M Adger M J Sasse M A Forth 1989 N Acetyl N Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon Organic Syntheses 67 187 doi 10 15227 orgsyn 067 0187 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link I Bruning R Grashey H Hauck R Huisgen H Seidl 1966 2 3 5 Triphenylisoxazolidine Organic Syntheses 46 127 doi 10 15227 orgsyn 046 0127 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link C S Marvel 1925 Cupferron Organic Syntheses 4 19 doi 10 15227 orgsyn 004 0019 Retrieved from https en wikipedia org w index php title Phenylhydroxylamine amp oldid 1217706858, wikipedia, wiki, book, books, library,
