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103543

Sigma-Aldrich

4-Nitroanisole

97%

Synonym(s):

1-Methoxy-4-nitrobenzene

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About This Item

Linear Formula:
O2NC6H4OCH3
CAS Number:
100-17-4
Molecular Weight:
153.14
Beilstein:
1865361
EC Number:
202-825-3
MDL number:
MFCD00007327
UNSPSC Code:
12352100
eCl@ss:
39032065
PubChem Substance ID:
24846610
NACRES:
NA.22

Assay

97%

form

solid

density

1.233 g/mL at 25 °C (lit.)

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
GHS08

Signal Word

Warning

Hazard Statements

H351,H412

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

Certificates of Analysis (COA)

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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
Song Chen et al.
Journal of economic entomology, 98(3), 943-946 (2005-07-19)
Cytochrome P450 monooxygenases are a major metabolic mechanism responsible for pyrethroid resistance in Helicoverpa armigera (Hübner) from Asia. Cytochrome P450-mediated O-demethylation activity toward p-nitroanisole (PNOD) of individual fourth instars was determined in five strains of H. armigera by using a
M S Romero-Cano et al.
Journal of controlled release : official journal of the Controlled Release Society, 82(1), 127-135 (2002-07-11)
The controlled release of 4-nitroanisole from polylactide nanoparticles with different morphologies is reported. Two theoretical equations have been used in an attempt to fit the experimental results. Good agreement between theory and experiment was found for short release time. The
V V Shumiantseva et al.
Voprosy meditsinskoi khimii, 44(4), 369-375 (1998-12-10)
Semisynthetic flavocytochromes, obtained by covalent binding of riboflavins with cytochrome P450 2B4, were able to catalyse H2O2-supported aniline p-hydroxylation, amidopyrine N-demethylation and p-nitroanisole O-dealkylation. Rates of these reactions were considerably higher than the rates of corresponding NAD(P)H-dependent reactions and comparable
H V Gelboin et al.
Biochemical pharmacology, 50(11), 1841-1850 (1995-11-27)
Cytochromes P450 3A3/4 are inordinately important P450 enzymes catalyzing the metabolism of a large variety of clinically useful drugs, steroids, and carcinogens. Two monoclonal antibodies, MAb 3-29-9 and MAb 275-1-2, were prepared to human P450 3A4 from mice immunized with
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