249319
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:
Molecular Weight:
154.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-236-8
Beilstein/REAXYS Number:
2210196
MDL number:
Assay:
98%
Quality Level
assay
98%
mp
150-154 °C (lit.)
functional group
nitro
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
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.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1A
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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)