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103543

Sigma-Aldrich

4-Nitroanisole

97%

Synonym(s):

1-Methoxy-4-nitrobenzene

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5 G
$33.60
25 G
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About This Item

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

$33.60

Available to ship onApril 22, 2025Details

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Quality Level

100

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[1].

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[2]. 4-Nitroanisole was used as carbon and energy supplement for the isolation of Rhodococcus strains[3].

Biochem/physiol Actions

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

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351,H412

Hazard Classifications

Aquatic Chronic 3 - Carc. 2

Storage Class

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

wgk_germany

WGK 1

flash_point_f

266.0 °F - closed cup

flash_point_c

130 °C - closed cup

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBF7314V
STBF4722V
STBD0772V
STBC8738V
STBC7426V

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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
D J Sequeira et al.
Biochimica et biophysica acta, 1207(2), 179-186 (1994-08-17)
The goal of this study was to examine the effect of duration of ethylbenzene exposure on cytochrome P-450-dependent activities. Male rats were treated with ethylbenzene by intraperitoneal injection for either 1 or 3 days, and microsomal preparations were examined for
Andrea Ciani et al.
Environmental science & technology, 39(17), 6712-6720 (2005-09-30)
Photodegradation is a key process in governing the residence time and fate of many agrochemicals in top soils. However, the basic knowledge of the photolytic transformation reactions of organic chemicals on soil surfaces is still very poor, particularly regarding the
A Schäfer et al.
Biodegradation, 7(3), 249-255 (1996-06-01)
Two Rhodococcus strains, R. opacus strain AS2 and R. erythropolis strain AS3, that were able to use 4-nitroanisole as the sole source of carbon and energy, were isolated from environmental samples. The first step of the degradation involved the O-demethylation
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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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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