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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

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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

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This Item
71158624350644110
N-Phenylhydroxylamine ≥95.0%

Sigma-Aldrich

671576

N-Phenylhydroxylamine

2-(Methylamino)phenol ≥97%

Sigma-Aldrich

711586

2-(Methylamino)phenol

2-Chloro-N,N-dimethylacetamide ≥97.0% (GC)

Sigma-Aldrich

24350

2-Chloro-N,N-dimethylacetamide

N-(2,3-Epoxypropyl)phthalimide ≥95.0%

Sigma-Aldrich

644110

N-(2,3-Epoxypropyl)phthalimide

assay

≥95.0%

assay

≥97%

assay

≥97.0% (GC)

assay

≥95.0%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

-

storage temp.

-

storage temp.

-

form

solid

form

crystals

form

liquid

form

solid

mp

80-84 °C

mp

89-94 °C

mp

-

mp

92-98 °C (lit.)

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.[1]
  • Isoxazolidines by reacting with aldehydes and α, β-unsaturated aldehydes via a three-component one-pot catalytic reaction.[2]
  • Tetrahydro-1,2-oxazines by treating with an aldehyde and cyclopropane via homo 3+2 dipolar cycloaddition reaction.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000453039
0000453039
BCCL0284
BCCJ8747
BCCH2810

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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
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)
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.
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