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Safety Information

671576

Sigma-Aldrich

N-Phenylhydroxylamine

≥95.0%

Synonym(s):

N-Hydroxyaniline, N-Hydroxybenzenamine

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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

671576-VAR:
671576-5G:
671576-1G:
671576-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL0284
BCCJ8747
BCCH2810
BCCG0719
BCCF4539

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Y Endo et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 114(8), 565-576 (1994-08-01)
The acid-catalyzed reaction of N-acyl- and N-sulfonylhydroxylamines with benzene proceeded smoothly to give C-C products; 2- and 4-hydroxybiphenyls. The reaction and the thermolysis of N-aryloxypyridinium salts involve common intermediates. The results of product analysis, the orientation of the reaction, effects
M F Khan et al.
Toxicological sciences : an official journal of the Society of Toxicology, 42(1), 64-71 (1998-05-30)
To elucidate the role of N-phenylhydroxylamine (PHA, N-hydroxylated metabolite of aniline) in the selective toxicity of aniline to the spleen, dose-dependent studies were conducted with PHA in rats. Male Sprague-Dawley rats were given four doses each (1 dose/day) of 0.025
A simple one-pot, three-component, catalytic, highly enantioselective isoxazolidine synthesis
Rios R, et al.
Tetrahedron Letters, 48(32), 5701-5705 (2007)
L Ciccoli et al.
Toxicology letters, 110(1-2), 57-66 (1999-12-11)
Incubation of rat erythrocytes with the hydroxylated metabolites of aniline and dapsone (4-4'-diaminodiphenylsulfone), phenylhydroxylamine and dapsone hydroxylamine, respectively, induced marked release of iron and methemoglobin formation. On the contrary, no release of iron nor methemoglobin formation was seen when the
Christine S Olver et al.
Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis, 24(3), 273-278 (2012-12-12)
Carboxyheme and metheme states modulate hemostasis in humans and other species. Further, carbon monoxide and/or nitric oxide production increase in inflammatory disorders involving the gastrointestinal tract, with associated hypercoagulability or hypocoagulability. In particular, the horse suffers both thrombotic or coagulopathic
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