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Merck
CN

103543

Sigma-Aldrich

4-Nitroanisole

97%

Synonym(s):

1-Methoxy-4-nitrobenzene

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About This Item

Linear Formula:
O2NC6H4OCH3
CAS Number:
Molecular Weight:
153.14
Beilstein:
1865361
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39032065
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

Assay

97%

form

solid

density

1.233 g/mL at 25 °C (lit.)

functional group

nitro

SMILES string

COc1ccc(cc1)[N+]([O-])=O

InChI

1S/C7H7NO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

InChI key

BNUHAJGCKIQFGE-UHFFFAOYSA-N

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General description

4-Nitroanisole undergoes photochemical nucleophilic aromatic substitution by hydroxide ion to form 4-methoxyphenol and 4-nitrophenol.

Application

4-Nitroanisole was used as probe to determine Π* of Kamlet-Taft solvent parameters and high pressure and supercritical water in the temperature range of 16-420 °C. 4-Nitroanisole was used as carbon and energy supplement for the isolation of Rhodococcus strains.

Biochem/physiol Actions

4-Nitroanisole is O-demethylated to 4-nitrophenol by human liver microsomes.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 3 - Carc. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

266.0 °F - closed cup

Flash Point(C)

130 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Vadim Samoilov et al.
Molecules (Basel, Switzerland), 25(7) (2020-04-15)
In this study approaches for chemical conversions of the renewable compounds 1,2-propanediol (1,2-PD) and 2,3-butanediol (2,3-BD) that yield the corresponding cyclic ketals and glycol ethers have been investigated experimentally. The characterization of the obtained products as potential green solvents and
Petr Klán et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 1(12), 1012-1016 (2003-03-29)
A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by a hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature
B C Jones et al.
Xenobiotica; the fate of foreign compounds in biological systems, 27(10), 1025-1037 (1997-11-19)
1. 4-Nitroanisole is O-demethylated to 4-nitrophenol by human liver microsomes. Kinetic studies indicate that this metabolic route is mediated by two cytochrome P450 isoforms, one with a K(m) = 2.1 microM and the other with a K(m) = 220 microM.
Y Sai et al.
Pharmacogenetics, 9(2), 229-237 (1999-06-22)
Cytochrome P450 (CYP) 2A6 is an important enzyme catalysing the metabolism of many drugs, procarcinogens and promutagens. Its role in human liver metabolism of coumarin, 4-nitroanisole, 4-nitrophenol and 7-ethoxycoumarin was analysed with an inhibitory monoclonal antibody (MAb) to CYP2A6. MAbs
Kimitaka Minami et al.
Physical chemistry chemical physics : PCCP, 8(19), 2257-2264 (2006-05-12)
Kamlet-Taft solvent parameters, pi*, of high pressure and supercritical water were determined from 16-420 degrees C based on solvatochromic measurements of 4-nitroanisole. For the measurements, an optical cell that could be used at high temperatures and pressures was developed with

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