671576
N-Phenylhydroxylamine
≥95.0%
Synonym(s):
N-Hydroxyaniline, N-Hydroxybenzenamine
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About This Item
Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
Molecular Weight:
109.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
assay
≥95.0%
form
solid
mp
80-84 °C
storage temp.
−20°C
SMILES string
ONc1ccccc1
InChI
1S/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H
InChI key
CKRZKMFTZCFYGB-UHFFFAOYSA-N
Application
N-Phenylhydroxylamine can be used as a starting material for the synthesis of:
- 2-alkylindoles by treating with aliphatic terminal alkynes using gold catalyst via sequential 3,3-rearrangements and cyclodehydrations.
- Isoxazolidines by reacting with aldehydes and α, β-unsaturated aldehydes via a three-component one-pot catalytic reaction.
- Tetrahydro-1,2-oxazines by treating with an aldehyde and cyclopropane via homo 3+2 dipolar cycloaddition reaction.
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes
Wang Y, et al.
Chemical Communications (Cambridge, England), 47(27), 7815-7817 (2011)
Copper-catalyzed amination of alkenes and ketones by phenylhydroxylamine.
Ho C-M and Lau T-C
New. J. Chem., 24(11), 859-863 (2000)
T P Bradshaw et al.
Free radical biology & medicine, 18(2), 279-285 (1995-02-01)
Previous studies have shown that incubation of rat red blood cells in vitro with phenylhydroxylamine (50-300 microM) induces rapid splenic sequestration of the red cells on reintroduction to isologous rats. EPR and the spin trapping agent, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), were utilized
Three-component homo 3+ 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1, 2-oxazines and FR900482 skeletal congeners
Young IS and Kerr MA
Organic Letters, 6(1), 139-141 (2004)
Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: synthesis of the tetracyclic core of nakadomarin A.
Young L S, et al.
Organic Letters, 7(5), 953-955 (2005)
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