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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

Quality Level

200

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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)
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)
4-Nitroaniline-picric acid (2/1)
Li Y-J
Acta Crystallographica Section E, Structure Reports Online, 65(10), o2566-o2566 (2009)
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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