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N-Phenylhydroxylamine: Difference between revisions

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Revision as of 08:52, 18 February 2011 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits removed Category:Aromatic amines; added Category:Anilines using HotCat← Previous edit Latest revision as of 20:06, 19 November 2024 edit undoGabldotink (talk | contribs)Extended confirmed users1,690 editsm →top: converted Template:Displaytitle to magic wordTags: Mobile edit Mobile app edit Android app edit App section source 
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⚫ {{DISPLAYTITLE:''N''-Phenylhydroxylamine}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 284344552
| Watchedfields = changed
⚫ | Name = Phenylhydroxylamine
⚫ | verifiedrevid = 414590802
| ImageFile = Phenylhydroxylamine.png | Name = ''N''-Phenylhydroxylamine
⚫ | ImageSize = 120px
| ImageName = Phenylhydroxylamine | ImageFileL1 = Phenylhydroxylamine.png
⚫ | ImageSizeL1 = 120px
| IUPACName = ''N''-phenylhydroxylamine | ImageAltL1 = Skeletal formula of phenylhydroxylamine
⚫ | OtherNames = ''beta''-henylhydroxylamine; ''N''-hydroxyaniline; phenylhydroxylamine; ''N''-hydroxybenzeneamine; hydroxylaminobenzene
| ImageFileR1 = Phenylhydroxylamine 3D ball.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSizeR1 = 130
⚫ | CASNo_Ref = {{cascite}}
| ImageAltR1 = Ball-and-stick model of the phenylhydroxylamine molecule
⚫ | CASNo = 100-65-2
| PIN = ''N''-Hydroxyaniline
⚫ | SMILES = ONC1=CC=CC=C1
⚫ | OtherNames = ''beta''-phenylhydroxylamine; phenylhydroxylamine; ''N''-hydroxybenzeneamine; hydroxylaminobenzene
⚫ | RTECS =
⚫ |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 100-65-2
⚫ | SMILES = ONC1=CC=CC=C1
| PubChem = 7518
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7237
| EINECS = 209-711-2
| InChI = 1/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H
| InChIKey = CKRZKMFTZCFYGB-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CKRZKMFTZCFYGB-UHFFFAOYSA-N
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28902
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C02720
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 282MU82Z9A
⚫ | RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>7</sub>NO | Formula = C<sub>6</sub>H<sub>7</sub>NO
| MolarMass = 109.1274 g/mol | MolarMass = 109.1274 g/mol
| Appearance = yellow needles | Appearance = yellow needles
| Density = | Density =
| Solubility = | Solubility =
| MeltingPt = 80-81 °C | MeltingPtC = 80 to 81
| BoilingPt = | MeltingPt_notes =
| pKa = | BoilingPt =
| pKa =
| MagSus = -68.2·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = | MolShape =
| CrystalStruct = | CrystalStruct =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| RPhrases = | HPhrases =
| SPhrases = | PPhrases =
| GHS_ref =
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = ], ] | OtherCompounds = ], ]
}} }}
}} }}


'''Phenylhydroxylamine''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>NHOH. It is an intermediate in the redox-related pair ] and ]. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or ''O''-phenylhydroxylamine, is C<sub>6</sub>H<sub>5</sub>ONH<sub>2</sub>. '''''N''-Phenylhydroxylamine''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>NHOH. It is an intermediate in the redox-related pair ] and ]. ''N''-Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or ''O''-phenylhydroxylamine.


==Preparation and derivatives== ==Preparation==
This compound can be prepared by the reduction of ] with zinc in the presence of NH<sub>4</sub>Cl followed by crystallization as yellowish needles from salt-saturated water.<ref>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).</ref><ref>{{OrgSynth | author = O. Kamm | title = Phenylhydroxylamine | collvol = 1 | collvolpages = 445| year = 1941 | prep = CV1P0445}}</ref> Alternatively, it can be prepared by transfer hydrogenation of C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub> using hydrazine as an H<sub>2</sub> source over a rhodium catalyst.<ref>{{OrgSynth | author = P. W. Oxley, B. M. Adger, M. J. Sasse, and M. A. Forth | title = N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon | collvol = 16 | collvolpages = 16| year = 1993 | prep = CV8P0016}}</ref> The product can be purified from contaminating NaCl by extraction into benzene followed by precipitation with petroleum ether. C<sub>6</sub>H<sub>5</sub>NHOH is unstable to heating, and in the presence of strong acids easily rearranges to ]. Oxidation of phenylhydroxylamine with ] is a useful method of preparation of ]. This compound can be prepared by the reduction of ] with zinc in the presence of NH<sub>4</sub>Cl.<ref>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)</ref><ref>{{cite journal|journal=Organic Syntheses| author = O. Kamm | title = Phenylhydroxylamine | volume = 4 | page = 57| year = 1941 | doi= 10.15227/orgsyn.004.0057}}</ref>


Alternatively, it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H<sub>2</sub> source over a rhodium ].<ref>{{cite journal|journal=Organic Syntheses| author = P. W. Oxley, B. M. Adger, M. J. Sasse, M. A. Forth | title = N-Acetyl-N-Phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon | volume = 67| page = 187| year = 1989| doi= 10.15227/orgsyn.067.0187}}</ref>
⚫ The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole:<ref>{{OrgSynth | author = I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl | title = 2,3,5-Triphenylisoxazolidine | collvol = 5 | collvolpages = 1124| year = 1973 | prep = CV5P1124}}</ref>

⚫ ::C<sub>6</sub>H<sub>5</sub>NHOH + C<sub>6</sub>H<sub>5</sub>CHO → C<sub>6</sub>H<sub>5</sub>N(O)=CHC<sub>6</sub>H<sub>5</sub> + H<sub>2</sub>O
==Reactions==
{{stack|], is prepared from phenylhydroxylamine.]]}}
Phenylhydroxylamine is unstable to heating, and in the presence of strong acids easily rearranges to ] via the ]. Oxidation of phenylhydroxylamine with ] gives ].

⚫ Like other hydroxylamines it will react with ]s to form ]s, illustrative is the condensation with benzaldehyde to form diphenylnitrone, a well-known ]:<ref>{{cite journal| author = I. Brüning, R. Grashey, H. Hauck, R. Huisgen, H. Seidl | title = 2,3,5-Triphenylisoxazolidine | journal = Organic Syntheses | volume = 46 | pages = 127| year = 1966 | doi = 10.15227/orgsyn.046.0127}}</ref>

⚫ :C<sub>6</sub>H<sub>5</sub>NHOH + C<sub>6</sub>H<sub>5</sub>CHO → C<sub>6</sub>H<sub>5</sub>N(O)=CHC<sub>6</sub>H<sub>5</sub> + H<sub>2</sub>O

Phenylhydroxylamine is attacked by NO<sup>+</sup> sources to give ]:<ref>{{cite journal|doi=10.15227/orgsyn.004.0019|title=Cupferron|journal=Organic Syntheses|year=1925|volume=4|pages=19|author=C. S. Marvel}}</ref>
:C<sub>6</sub>H<sub>5</sub>NHOH + C<sub>4</sub>H<sub>9</sub>ONO + NH<sub>3</sub> → NH<sub>4</sub> + C<sub>4</sub>H<sub>9</sub>OH


==References== ==References==
{{reflist}} {{reflist}}


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