“Phenylhydroxylamine”的意思、由来-开放百科全书

词条

Phenylhydroxylamine

释义

Preparation
Reactions
References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 414590802
| Name = Phenylhydroxylamine
| ImageFileL1 = Phenylhydroxylamine.png
| ImageSizeL1 = 120px
| ImageAltL1 = Skeletal formula of phenylhydroxylamine
| ImageFileR1 = Phenylhydroxylamine 3D ball.png
| ImageSizeR1 = 130
| ImageAltR1 = Ball-and-stick model of the phenylhydroxylamine molecule
| IUPACName = N-phenylhydroxylamine
| OtherNames = beta-phenylhydroxylamine; N-hydroxyaniline; phenylhydroxylamine; N-hydroxybenzeneamine; hydroxylaminobenzene
|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
| Formula = C₆H₇NO
| MolarMass = 109.1274 g/mol
| Appearance = yellow needles
| Density =
| Solubility =
| MeltingPtC = 80 to 81
| MeltingPt_notes =
| BoilingPt =
| pKa =
| MagSus = -68.2·10⁻⁶ cm³/mol
|Section3={{Chembox Structure
| MolShape =
| CrystalStruct =
| Dipole =
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPt =
| RPhrases =
| SPhrases =
|Section8={{Chembox Related
| OtherCompounds = hydroxylamine, nitrosobenzene
}}

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.

Preparation

This 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

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.

The compound condenses with benzaldehyde to form diphenylnitrone, a well-known 1,3-dipole:^[4]

C₆H₅NHOH + C₆H₅CHO → C₆H₅N(O)=CHC₆H₅ + H₂O

References

1. ^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).
2. ^{{cite journal|journal=Organic Syntheses| author = O. Kamm | title = Phenylhydroxylamine | volume = 4 | page = 57| year = 1941 | doi= 10.15227/orgsyn.004.0057}}
3. ^{{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}}
4. ^{{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}}

1 : Hydroxylamines

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