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671576

Sigma-Aldrich

N-Phenylhydroxylamine

≥95.0%

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Synonym(s):
N-Hydroxyaniline, N-Hydroxybenzenamine
Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
100-65-2
Molecular Weight:
109.13
EC Number:
202-875-6
MDL number:
MFCD00045718
PubChem Substance ID:
329760431
NACRES:
NA.22

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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C C Somerville et al.
Journal of bacteriology, 177(13), 3837-3842 (1995-07-01)
Pseudomonas pseudoalcaligenes JS45 grows on nitrobenzene as a sole source of carbon, nitrogen, and energy. The catabolic pathway involves reduction to hydroxylaminobenzene followed by rearrangement to o-amino-phenol and ring fission (S. F. Nishino and J. C. Spain, Appl. Environ. Microbiol.
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
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
M M Shah et al.
Biochemical and biophysical research communications, 241(3), 794-796 (1998-01-22)
Nitrobenzene was reduced in a solution containing ferredoxin NADP oxidoreductase (FNR) from spinach leaves and NADPH generating system. The product of nitrobenzene was identified as phenylhydroxylamine (PHA) on 1:1 basis.
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)
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