Skip to Content
MilliporeSigma
All Photos(1)

Documents

671576

Sigma-Aldrich

N-Phenylhydroxylamine

≥95.0%

Synonym(s):

N-Hydroxyaniline, N-Hydroxybenzenamine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
100-65-2
Molecular Weight:
109.13
EC Number:
202-875-6
MDL number:
MFCD00045718
UNSPSC Code:
12352100
PubChem Substance ID:
329760431
NACRES:
NA.22

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

Related Categories

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
Vance G Nielsen et al.
Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis, 22(8), 657-661 (2011-08-09)
Cigarette smoking is associated with plasmatic hypercoagulability, and carbon monoxide has been demonstrated to enhance coagulation by binding to a fibrinogen-bound heme. Our objective was to design and test a redox-based method to detect carboxyhemefibrinogen. Normal, pooled, citrated plasma was
Lloyd J Nadeau et al.
Applied and environmental microbiology, 69(5), 2786-2793 (2003-05-07)
Hydroxylamino aromatic compounds are converted to either the corresponding aminophenols or protocatechuate during the bacterial degradation of nitroaromatic compounds. The origin of the hydroxyl group of the products could be the substrate itself (intramolecular transfer mechanism) or the solvent water
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service