4-Nitrophenol
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| 4-Nitrophenol | |
|---|---|
| IUPAC name | 4-nitrophenol |
| Other names | p-nitrophenol 4-hydroxynitrobenzene |
| Identifiers | |
| CAS number | |
| SMILES | OC1=CC=C([N+]([O-])=O)C=C1 |
| Properties | |
| Molecular formula | C6H5NO3 |
| Molar mass | 139.11 |
| Appearance | colorless or yellow pillars |
| Melting point |
113–114 °C |
| Boiling point |
279 °C |
| Solubility in water | 10 g/L (15 °C) 11.6 g/L (20 °C) 16 g/L (25 °C) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
4-Nitrophenol is a phenolic compound that has a nitro group at the opposite position of hydroxy group on the benzene ring. Also called p-nitrophenol or 4-hydroxynitrobenzene. Its molecular formula is C6H5NO3 and CAS registry number is 100-02-7.
Properties
4-Nitrophenol shows two polymorphs in 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 is existing as a mixture of these two forms.
In solution, 4-nitrophenol has a dissociation constant (pKa) of 7.08 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
It is believed that aerobic decomposition of 4-nitrophenol in an environment is not very good. Bioaccumulation of this compound is considered to rarely occur. Mainly, 4-nitrophenol is used as the precursor for the preparation of phenetidine and acetophenetidine, indicator, and raw material of fungicides.
In the peptide synthesis, carboxylate ester derivatives of 4-nitrophenol may served as activated components for a constraction of an amide moieties.
Toxicity
4-Nitrophenol irritates eyes, skin, and respiratory tract; and may cause the inflammation of those parts. It makes delayed intaraction with blood and formes methaemoglobin that is responsible for methemoglobinemia, which may cause cyanosis, confusion, and unconsciousness. When ingested, one will get abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. LD50: mouse, p.o. 282 mg/kg; rat, p.o. 202 mg/kg.
See also
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
