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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Bifu Liu et al.
Chemical communications (Cambridge, England), 48(93), 11446-11448 (2012-10-23)
A robust route to 4-amine-benzo[b][1,4]oxazepines relying upon a palladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides has been developed. This chemistry presumably proceeds through the migratory insertion of isocyanides into the vinyl-palladium intermediate as a key step.
Anangamohan Panja et al.
Dalton transactions (Cambridge, England : 2003), 42(14), 5068-5075 (2013-02-12)
A bis(imido)-bridged dinuclear cobalt(III) complex, [Co2(amp)2(μ-imp)2Cl2]Cl2·2H2O () [amp = 2-aminomethylpyridine; imp = 2-iminomethylpyridine anion], was synthesized by the reaction of cobalt(II) chloride with 2-aminomethylpyridine in the presence of alkaline hydrogen peroxide at room temperature. X-ray crystallography reveals that both the
Ru Chen et al.
Organic & biomolecular chemistry, 9(22), 7675-7679 (2011-09-23)
A palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates using Cu(OAc)(2)·H(2)O as oxidant has been discovered. The reaction proceeded well for a range of different substrates under oxidative conditions. A series of aryl-substituted azoles have been synthesized in moderate
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