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249319

Sigma-Aldrich

4-Amino-3-nitrophenol

98%

Synonym(s):

4-Hydroxy-2-nitroaniline

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About This Item

Linear Formula:
H2NC6H3(NO2)OH
CAS Number:
610-81-1
Molecular Weight:
154.12
Beilstein/REAXYS Number:
2210196
EC Number:
210-236-8
MDL number:
MFCD00066310
UNSPSC Code:
12352100
PubChem Substance ID:
24854986
NACRES:
NA.22

Quality Level

100

assay

98%

mp

150-154 °C (lit.)

SMILES string

Nc1ccc(O)cc1[N+]([O-])=O

InChI

1S/C6H6N2O3/c7-5-2-1-4(9)3-6(5)8(10)11/h1-3,9H,7H2

InChI key

IQXUIDYRTHQTET-UHFFFAOYSA-N

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Application

4-Amino-3-nitrophenol was used in the synthesis of benzimidazole based Factor Xa (trypsin-like serine protease) inhibitors and 4-(4-amino-3-nitrophenoxy)phthalonitrile. It was also employed as matrix during visible matrix-assisted laser desorption/ionization mass spectrometry.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1A

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis, characterization, and electrical, electrochemical and gas sensing properties of a novel cyclic borazine derivative containing three phthalocyaninato zinc (II) macrocycles.
Ozer M, et al.
Synt. Metals, 155(1), 222-231 (2005)
Lorianne R Shultz et al.
Molecules (Basel, Switzerland), 25(1) (2019-12-29)
Para-, or 4-nitrophenol, and related nitroaromatics are broadly used compounds in industrial processes and as a result are among the most common anthropogenic pollutants in aqueous industrial effluent; this requires development of practical remediation strategies. Their catalytic reduction to the
Z Zhao et al.
Bioorganic & medicinal chemistry letters, 10(9), 963-966 (2000-06-15)
Inhibitors based on the benzimidazole scaffold showed subnanomolar potency against Factor Xa with 500-1000-fold selectivity against thrombin and 50-100-fold selectivity against trypsin. The 2-substituent on the benzimidazole ring had a strong impact on the FXa inhibitory activity. Crystallography studies suggest
Lee Chuin Chen et al.
Rapid communications in mass spectrometry : RCM, 21(24), 4129-4134 (2007-11-21)
Visible matrix-assisted laser desorption/ionization (VIS-MALDI) was performed using 2-amino-3-nitrophenol as matrix. The matrix is of near-neutral pH, and has an optical absorption band in the near-UV and visible region. A frequency-doubled Nd:YAG laser operated at 532 nm wavelength was used
Wendell Ho-Tin Law et al.
ChemMedChem, 9(6), 1316-1329 (2014-03-20)
We present a new class of phosphorescent cyclometalated iridium(III) bipyridyl-phenylenediamine complexes [Ir(N^C)2 (bpy-DA)](PF6 ) (bpy-DA=4-(N-(2-amino-5-methoxyphenyl)aminomethyl)-4'-methyl-2,2'-bipyridine; HN^C=2-(2,4-difluorophenyl)pyridine (Hdfppy) (1 a), 2-phenylpyridine (Hppy) (2 a), 2-phenylquinoline (Hpq) (3 a), 2-phenylcinchoninic acid methyl ester (Hpqe) (4 a)) and their triazole counterparts [Ir(N^C)2 (bpy-T)](PF6

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