3-Nitrophenol

Chemical properties

yellow to brown crystalline powder

The Uses of 3-Nitrophenol

3-Nitrophenol is a chemical reagent used in various organic syntheses. Used in the synthesis of RAGE inhibitors via the etherification of phenols. Also used in the synthesis of kinase inhibitors again st epidermal growth factor receptor T790M mutation.

The Uses of 3-Nitrophenol

As indicator in 0.3% solution in 50% alcohol. pH: 6.8 colorless, 8.6 yellow.

The Uses of 3-Nitrophenol

3-Nitrophenol is a chemical reagent used in various organic syntheses. Used in the synthesis of RAGE inhibitors via the etherification of phenols. Also used in the synthesis of kinase inhibitors against epidermal growth factor receptor T790M mutation.

What are the applications of Application

3-Nitrophenol is a chemical reagent used in various organic syntheses

Definition

ChEBI: A member of the class of 3-nitrophenols that is phenol in which one of the hydrogens that is meta to the hydroxy group has been replaced by a nitro group.

Production Methods

3-Nitroaniline is diazotized in aqueous sulfuric acid and then hydrolyzed by being added gradually to boiling dilute sulfuric acid. The crude product solidifies on cooling and is filtered off in 90 % yield.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 5117, 1995 DOI: 10.1016/0040-4039(95)00963-D

General Description

Colorless to pale yellow crystalline solid. Sinks in and mixes with water.

Air & Water Reactions

Water insoluble.

Reactivity Profile

3-Nitrophenol is a light-yellow, crystalline material, toxic and irritant. When heated to decomposition 3-Nitrophenol emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.

Hazard

Toxic by ingestion.

Health Hazard

INHALATION: Inhalation or ingestion causes headaches, drowsiness, nausea, and blue color in lips, ears, and finger nails (cyanosis). EYES: Contact with eyes causes irritation. SKIN: Can be absorbed through intact skin to give same symptoms as for inhalation.

Fire Hazard

Special Hazards of Combustion Products: Dangerous toxic fumes of NO x

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also other nitrophenol entries.

Purification Methods

Crystallise 3-nitrophenol from water, CHCl3, CS2, EtOH or pet ether (b 80-100o), and dry it under vacuum over P2O5 at room temperature. It can also be distilled at low pressure. The 4-nitrobenzoate had m 174o (from EtOH). [Beilstein 6 IV 1269.]