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A71301

Sigma-Aldrich

2-Aminophenol

99%

Synonym(s):

(2-Hydroxyphenyl)amine, 1-Hydroxy-2-aminobenzene, 2-Amino-1-hydroxybenzene, 2-Aminophenol, 2-Aminophenyl alcohol, 2-Hydroxyaniline, 2-Hydroxybenzenamine, o-Aminohydroxybenzene, o-Hydroxyaniline, o-Hydroxyphenylamine

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About This Item

Linear Formula:
H2NC6H4OH
CAS Number:
95-55-6
Molecular Weight:
109.13
Beilstein:
606075
EC Number:
202-431-1
MDL number:
MFCD00007690
UNSPSC Code:
12352100
PubChem Substance ID:
24891176
NACRES:
NA.22

Assay

99%

form

powder

mp

170-175 °C (lit.)

SMILES string

Nc1ccccc1O

InChI

1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2

InChI key

CDAWCLOXVUBKRW-UHFFFAOYSA-N

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Application

2-Aminophenol can be used in the synthesis of:
  • 2-Oxazolidinone derivatives by reacting with β-aminoalcohols in presence of Pd/C-I2 as a catalyst via oxidative cyclocarbonylation.
  • Schiff base transition metal(II) complexes with salicylidene-4-aminoantipyrine.
  • 2-Arylbenzoxazoles with aldehydes catalyzed by activated carbon in presence of oxygen atmosphere.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302 + H332,H341

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Muta. 2

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

334.4 °F - closed cup

Flash Point(C)

168 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis of 2-oxazolidinone catalyzed by palladium on charcoal: a novel and highly effective heterogeneous catalytic system for oxidative cyclocarbonylation of β -aminoalcohols and 2-aminophenol.
Li F and Xia C
J. Catal., 227(2), 542-546 (2004)
Synthesis, spectroscopic characterization, redox, and biological screening studies of some Schiff base transition metal (II) complexes derived from salicylidene-4-aminoantipyrine and 2-aminophenol/2-aminothiophenol.
Raman N, et al.
Synth. React. Inorg. Met.-Org. Chem. , 31(7), 1249-1270 (2001)
Michael M Bittner et al.
Journal of the American Chemical Society, 134(12), 5460-5463 (2012-03-16)
The oxidative ring cleavage of aromatic substrates by nonheme Fe dioxygenases is thought to involve formation of a ferrous-(substrate radical) intermediate. Here we describe the synthesis of the trigonal-bipyramdial complex Fe((Ph2)Tp)(ISQ(tBu)) (2), the first synthetic example of an iron(II) center
Yoshinori Endo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(43), 13609-13613 (2012-09-13)
Aerobic oxidation: in a biomimetic approach, a mixture of redox catalysts forms couples that effect the aerobic oxidation of a mixture of benzylamine and 2-aminophenol derivatives to give the corresponding benzoxazoles. This biomimetic oxidation proceeds smoothly under mild conditions and
Ericsson D Coy et al.
Organic letters, 12(9), 1976-1979 (2010-03-27)
An efficient and facile synthesis of trans-dihydrobenzofurans has been accomplished from o-aminophenols and phenylpropenes via a novel (one-pot) diastereoselective Pd-catalyzed oxyarylation reaction. The development and optimization of this method is described.
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