2-Nitro-1-naphthol
[CAS# 607-24-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: 2-Nitro-1-naphthol
• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.17
• CAS Registry Number: 607-24-9
• EC Number: 210-131-7
• SMILES: C1=CC=C2C(=C1)C=CC(=C2O)[N+](=O)[O-]

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 123-125 °C
• Index of Refraction: 1.714, Calc.^*
• Boiling Point: 336.7±15.0 °C (760 mmHg), Calc.^*
• Flash Point: 149.9±8.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H334-H335-H4112
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

2-Nitro-1-naphthol is a chemical compound characterized by the presence of a nitro group at the second position of the naphthol structure. It is a derivative of naphthalene, which is a polycyclic aromatic hydrocarbon, and the addition of a nitro group introduces unique chemical properties that enhance its utility in various applications. The compound was first synthesized in the early 20th century during a period of extensive research into nitroaromatic compounds, which were gaining attention for their diverse applications in dye chemistry, pharmaceuticals, and agrochemicals.

The synthesis of 2-nitro-1-naphthol typically involves the nitration of 1-naphthol using a mixture of concentrated nitric and sulfuric acids. This process selectively introduces a nitro group at the 2-position, resulting in the formation of the desired compound. The reaction conditions must be carefully controlled to ensure the desired regioselectivity and to minimize the formation of unwanted by-products.

One of the primary applications of 2-nitro-1-naphthol is in the dye industry, where it serves as an important intermediate for the synthesis of various dyes and pigments. The compound's ability to participate in coupling reactions with diazonium salts allows for the production of azo dyes, which are widely used in textiles, inks, and plastics. These azo dyes are valued for their vivid colors and excellent fastness properties, making 2-nitro-1-naphthol a crucial component in the manufacturing of colorants.

In addition to its role in dye synthesis, 2-nitro-1-naphthol has found applications in the pharmaceutical industry. It acts as a key intermediate in the synthesis of several biologically active compounds. The nitro group can be reduced to an amino group, leading to the formation of aminonaphthol derivatives, which exhibit a range of pharmacological activities. This transformation expands the potential applications of 2-nitro-1-naphthol in drug development and medicinal chemistry.

Moreover, 2-nitro-1-naphthol is utilized as a reagent in various chemical reactions. Its reactivity allows it to participate in electrophilic substitution reactions, making it useful for the synthesis of more complex organic molecules. This versatility has positioned 2-nitro-1-naphthol as a valuable compound in organic synthesis, where it contributes to the development of new materials and chemical entities.

Research into the environmental impact of 2-nitro-1-naphthol and its derivatives has become increasingly important, particularly given the potential toxicity associated with nitroaromatic compounds. Studies have focused on understanding the degradation pathways and environmental behavior of this compound to mitigate any adverse effects. Efforts to develop greener synthesis routes and safer alternatives are ongoing, reflecting a broader trend in the chemical industry towards sustainability and reduced environmental impact.

In summary, 2-nitro-1-naphthol is a significant chemical compound with a variety of applications in the dye industry, pharmaceuticals, and organic synthesis. Its unique chemical properties, particularly the presence of the nitro group, enhance its reactivity and utility as an intermediate in various chemical processes. Ongoing research into its safety and environmental impact underscores the importance of responsible chemical management and the development of sustainable practices in its production and application.

References

2022. Potentials of N-(2, 4-dinitro-1-naphthyl)-p-toluenesulphonamide and 2, 4-dinitro-1-naphthol as novel charge transfer acceptors in pharmaceutical analysis of some quinolones and cephalosporins. Future Journal of Pharmaceutical Sciences, 8(1).
DOI: 10.1186/s43094-022-00407-7

2007. Complexes of nitronaphthols with aluminum bromide. Russian Journal of Applied Chemistry, 80(6).
DOI: 10.1134/s107042720706033x

1992. Improved synthesis of several methoxynitronaphthalenes. Monatshefte für Chemie / Chemical Monthly, 123(6).
DOI: 10.1007/bf00816858