4-Nitrophenol

4-Nitrophenol
Coarse yellow crystals
Names
IUPAC name
4-Nitrophenol
Other names
p-Nitrophenol
para-Nitrophenol
4-Hydroxynitrobenzene
PNP
Identifiers
100-02-7 YesY
ChEBI CHEBI:16836 YesY
ChEMBL ChEMBL14130 YesY
ChemSpider 955 YesY
DrugBank DB04417 YesY
Jmol interactive 3D Image
Image
KEGG C00870 YesY
PubChem 980
UNII Y92ZL45L4R YesY
Properties
C6H5NO3
Molar mass 139.11 g·mol−1
Appearance Colorless or yellow pillars
Melting point 113 to 114 °C (235 to 237 °F; 386 to 387 K)
Boiling point 279 °C (534 °F; 552 K)
10 g/L (15 °C)
11.6 g/L (20 °C)
16 g/L (25 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring.

Properties

4-Nitrophenol shows two polymorphs in the crystalline state. The alpha-form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta-form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms.

In solution, 4-nitrophenol has a dissociation constant (pKa) of 7.16 at 22 °C. Solution of 4-nitrophenol alone appears colorless or pale yellow, whereas its phenolic salts tend to develop a bright yellow color. This color-changing property makes this compound useful as a pH indicator.

Uses

4-Nitrophenol is an intermediate in the synthesis of paracetamol. It is reduced to 4-aminophenol, then acetylated with acetic anhydride.[1]

4-Nitrophenol is used as the precursor for the preparation of phenetidine and acetophenetidine, indicators, and raw materials for fungicides. Bioaccumulation of this compound rarely occurs.

In peptide synthesis, carboxylate ester derivatives of 4-nitrophenol may serve as activated components for construction of amide moieties.

Uses of nitrophenol derivatives

4-Nitrophenol is a product of the enzymatic cleavage of several substrates such as 4-nitrophenyl acetate (used as a substrate for carbonic anhydrase), and 4-nitrophenyl-β-D-glucopyranoside and other sugar derivatives which are used to assay various glycosidase enzymes. Amounts of 4-nitrophenol produced by a particular enzyme (alkaline phosphatase) in the presence of its corresponding substrate can be measured with a spectrophotometer at or around 405 nm (ε = 18.1 mM-1 cm-1) [2] and used as a proxy measurement for the amount of the enzyme activity in the sample. Accurate measurement of enzyme activity requires that the 4-nitrophenol product is fully deprotonated, existing as 4-nitrophenolate, as 4-nitrophenol has a weak absorbance at 405 nm (ε = 0.2 mM-1 cm-1).[2]

A common mistake in measuring enzyme activity using these substrates is to perform the assays at neutral or acidic pH without considering that only part of the chromophoric product is ionised. The problem can be overcome by stopping the reaction with NaOH or other strong base (which converts all product into 4-nitrophenoxide; final pH must be > ca. 9.2 to ensure more than 99% of the product is ionised). Alternatively enzyme activity can be measured at 348 nm, the isosbestic point for 4-nitrophenol/4-nitrophenoxide (ε = 5.4 mM−1·cm−1).

Toxicity

4-Nitrophenol irritates the eyes, skin, and respiratory tract.[3] It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methaemoglobin which is responsible for methemoglobinemia, potentially causing cyanosis, confusion, and unconsciousness.[3] When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. The LD50 in mice is 282 mg/kg and in rats is 202 mg/kg (p.o.).

See also

References

  1. ↑ Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.
  2. 1 2 "High-Purity 4-Nitrophenol: Purification, Characterization, and Specifications for Use as a Spectrophotometric Reference Material". Clinical Chemistry. July 1980.
  3. 1 2 "Toxicological Profile For Nitrophenols" (PDF). Agency for Toxic Substances and Disease Registry, U.S. Public Health Service. July 1992.
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