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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:
2210196
EC Number:
210-236-8
MDL number:
MFCD00066310
UNSPSC Code:
12352100
PubChem Substance ID:
24854986
NACRES:
NA.22

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

Signal Word

Warning

Hazard Statements

H302,H317,H319,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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)
Qiaoran Liu et al.
Journal of colloid and interface science, 569, 12-21 (2020-02-26)
Organic contaminants, dyes and antibiotics, discharged in wastewater systems, have posed great threats to the sustainability of the ecosystem. This study was performed to prepare graphitic carbon nitride (GCN) nanocomposites modified by nanocarbons, including carbon quantum dots (CQD), carbon nanotube
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
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