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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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About This Item

Linear Formula:
O2NC6H4NH2
CAS Number:
100-01-6
Molecular Weight:
138.12
Beilstein:
508690
EC Number:
202-810-1
MDL number:
MFCD00007858
UNSPSC Code:
12352100
eCl@ss:
39032009
PubChem Substance ID:
24850683
NACRES:
NA.22

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

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. 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. Photocatalytic degradation of 4-nitroaniline in the presence of TiO2 suspensions in a batch and continuous annular reactor has been studied.

Application

4-Nitroaniline can be used to prepare:
  • p

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

Product of chromogenic reactions.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
4-Nitroaniline-picric acid (2/1)
Li Y-J
Acta Crystallographica Section E, Structure Reports Online, 65(10), o2566-o2566 (2009)
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)
Facile synthesis of spin-coated poly (4-nitroaniline) thin film: Structural and optical properties
Abed-Elmageed AAI, et al.
Optical Materials, 109(6), 110378-110378 (2020)
High efficient photocatalytic reduction of 4-nitroaniline to p-phenylenediamine over microcrystalline SrBi2Nb2O9
Wu W, et al.
Catalysis Communications, 17, 39-42 (2012)
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