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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
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
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
H V Gelboin et al.
Chemical research in toxicology, 9(6), 1023-1030 (1996-09-01)
A panel of 17 hybridomas producing (MAbs) against human cytochrome P450 2E1 (h2E1) was generated by immunizing mice with baculovirus-expressed h2E1. All 17 hybridoma clones gave positive ELISA or immunoblots with either baculovirus-or vaccinia virus-expressed h2E1. Two of the latter
V V Shumyantseva et al.
Biochemistry and molecular biology international, 45(1), 171-179 (1998-06-23)
Semisynthetic flavocytochromes, obtained by covalent binding of riboflavin with cytochromes P450 2B4, were able to catalyze the H2O2-mediated reactions of aniline p-hydroxylation, aminopyrine N-demethylation and p-nitroanizole' O-dealkylation. The rates of the flavocytochrome-catalyzed, H2O2-supported reactions far exceeded those of the appropriate
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