4-Hydroxy-3-nitrobenzyl alcohol
[CAS# 41833-13-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 4-Hydroxy-3-nitrobenzyl alcohol
• Synonyms: 4-(hydroxymethyl)-2-nitrophenol
• Molecular Formula: C₇H₇NO₄
• Molecular Weight: 169.13
• CAS Registry Number: 41833-13-0
• EC Number: 674-171-0
• SMILES: C1=CC(=C(C=C1CO)[N+](=O)[O-])O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 96-97 ºC (Expl.)
• Index of Refraction: 1.645, Calc.^*
• Boiling Point: 341.3±27.0 ºC (760 mmHg), Calc.^*
• Flash Point: 156.6±12.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

4-Hydroxy-3-nitrobenzyl alcohol is an organic compound with the molecular formula C7H7NO4, and it belongs to the family of nitro-substituted aromatic alcohols. The substance is characterized by the presence of a hydroxyl group (-OH) and a nitro group (-NO2) on the benzene ring, at the 4 and 3 positions, respectively. This configuration plays a key role in the chemical behavior and reactivity of the compound, making it useful in a variety of chemical and industrial applications.

The discovery of 4-hydroxy-3-nitrobenzyl alcohol is part of ongoing research into nitrobenzene derivatives, which have been studied extensively for their reactivity and potential for use in organic synthesis. The compound was first synthesized in the mid-20th century as part of efforts to develop more effective intermediates for pharmaceuticals, agrochemicals, and other industrial products. Its structure, with its hydroxyl and nitro functional groups, makes it particularly valuable as a building block in complex chemical synthesis.

In terms of applications, 4-hydroxy-3-nitrobenzyl alcohol finds its primary use as a precursor in the synthesis of more complex molecules. It serves as an important intermediate in the production of biologically active compounds, especially those involved in drug design. The presence of the nitro group allows for reactions such as reduction, nucleophilic substitution, or coupling with other organic molecules to create various therapeutic agents. Additionally, the hydroxyl group provides opportunities for further functionalization, allowing the compound to be adapted for a variety of synthetic pathways.

The compound has been utilized in the synthesis of certain pharmaceuticals, particularly in the development of anti-cancer and anti-inflammatory agents. Due to its structural features, it also shows promise in the creation of materials for electronic and optical applications. Research has indicated that nitro-containing aromatic alcohols like 4-hydroxy-3-nitrobenzyl alcohol possess antioxidant properties, which could be beneficial in the treatment of oxidative stress-related diseases.

In recent years, the compound has also been explored for its potential in the synthesis of functionalized polymers. Due to its ability to participate in a wide range of chemical reactions, 4-hydroxy-3-nitrobenzyl alcohol has been considered for use in the development of novel materials with specific properties for use in electronics, coatings, and specialty chemicals.

Overall, 4-hydroxy-3-nitrobenzyl alcohol is a valuable intermediate in the chemical and pharmaceutical industries, with significant potential in drug development, material science, and other fields. As research continues, new applications for this versatile compound may emerge, making it a promising substance for future innovations.