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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

Quality Level

200

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

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.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

A71301-5KG:
A71301-VAR:
A71301-100G:
A71301-500G:
A71301-5G:
A71301-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3085
STBK4803
STBK3153
STBJ2458
STBH1563

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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)
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
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
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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