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185310

Sigma-Aldrich

4-Nitroaniline

≥99%

Synonym(s):

1-Amino-4-nitrobenzene, 4-Amino-1-nitrobenzene, 4-Nitro-1-aminobenzene, 4-Nitrobenzenamine, p-Aminonitrobenze

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5 G
€25.50
100 G
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500 G
€78.50

About This Item

Linear Formula:
O2NC6H4NH2
CAS Number:
Molecular Weight:
138.12
Beilstein:
508690
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39032009
PubChem Substance ID:
NACRES:
NA.22

€25.50


Estimated to ship on01 April 2025


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Quality Level

Assay

≥99%

form

powder or crystals

bp

260 °C/100 mmHg (lit.)

mp

146-149 °C (lit.)

solubility

ethanol: soluble 25 mg/mL, slightly hazy, yellow to brownish-yellow
water: slightly soluble

functional group

nitro

SMILES string

Nc1ccc(cc1)[N+]([O-])=O

InChI

1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

InChI key

TYMLOMAKGOJONV-UHFFFAOYSA-N

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General description

4-Nitroaniline forms molecular adducts with 4-amino benzoic acid[1]. It reacts with nitrite ion in hydrochloric acid medium to form 4-nitrophenyldiazonium chloride, which couples with naphth-1-ol in alkaline medium to give a purple azo dye[2]. Photocatalytic degradation of 4-nitroaniline in the presence of TiO2 suspensions in a batch and continuous annular reactor has been studied[3].

Application

4-Nitroaniline can be used to prepare:
  • p

  • -Phenylenediamine using various catalytic systems.[4][5]
  • Poly(4-nitroaniline) thin films for optoelectronic applications.[6]
  • An adduct with picric acid.[7]
  • A crystalline N-(4-nitrophenyl)-β-alanine by reacting with acrylic acid.[8]

Product of chromogenic reactions.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

415.4 °F - closed cup

Flash Point(C)

213.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Crystal and molecular structure of N-(4-nitrophenyl)-?-alanine-Its vibrational spectra and theoretical calculations
Marchewka MK, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 79(4), 758-766 (2011)
A simple and highly efficient route for the preparation of p-phenylenediamine by reducing 4-nitroaniline over commercial CdS visible light-driven photocatalyst in water
Wu W, et al.
Green Chemistry, 14(6), 1705-1709 (2012)
Extraction-spectrophotometric determination of sub-microgram amounts of nitrite using 4-nitroaniline and naphth-1-ol.
Baveja AK, et al.
Analyst, 106(1266), 955-959 (1981)
Photocatalytic degradation of 4-nitroaniline using solar and artificial UV radiation.
Gautam S, et al.
Chemical Engineering Journal, 110(1), 129-137 (2005)
4-Nitroaniline-picric acid (2/1)
Li Y-J
Acta Crystallographica Section E, Structure Reports Online, 65(10), o2566-o2566 (2009)

Questions

1–2 of 2 Questions  
  1. 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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  2. 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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