3,5-Dinitrobenzoic acid
[CAS# 99-34-3]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: 3,5-Dinitrobenzoic acid
• Molecular Formula: C₇H₄N₂O₆
• Molecular Weight: 212.12
• CAS Registry Number: 99-34-3
• EC Number: 202-751-1
• SMILES: C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])C(=O)O

Properties

• Water solubility: 1350 mg/L (25 °C)
• Density: 1.7±0.1 g/cm³, Calc.^*, 1.68 g/mL (Expl.)
• Melting point: 204-206 °C (Expl.)
• Index of Refraction: 1.658, Calc.^*
• Boiling Point: 395.5±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 179.2±13.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H413
• Safety Statements: P264-P264+P265-P270-P273-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Flammable solids	Flam. Sol.	2	H228

Discovery and Applications

3,5-Dinitrobenzoic acid is a chemical compound with the molecular formula C7H4N2O4. It is a derivative of benzoic acid, featuring two nitro groups (-NO2) attached at the 3- and 5-positions of the benzene ring. The compound appears as a yellow crystalline solid and is known for its use in various chemical and industrial applications.

The discovery of 3,5-dinitrobenzoic acid stems from the broader exploration of nitrobenzoic acids, which are important intermediates in organic chemistry. Nitrobenzoic acids, including 3,5-dinitrobenzoic acid, have been studied extensively due to their role in the synthesis of various chemical compounds and their applications in the production of explosives, dyes, and pharmaceuticals. The nitro group is a powerful electron-withdrawing substituent, which influences the chemical reactivity and properties of the compound, making it valuable for specific chemical processes.

3,5-Dinitrobenzoic acid has found use primarily in organic synthesis. It serves as a precursor or intermediate in the synthesis of various other chemical compounds. For example, it can be involved in the preparation of aromatic amines, which are important for the production of dyes and pharmaceuticals. The nitro group in 3,5-dinitrobenzoic acid can undergo reduction to form amines, which can further react to produce other desired products. These reactions take advantage of the strong electron-withdrawing nature of the nitro group, making the compound useful in various synthetic pathways.

In addition to its role in synthesis, 3,5-dinitrobenzoic acid has applications in the field of materials science. It has been studied for use in the development of certain polymers and resins, where its nitro group contributes to the material's properties, such as increased stability or reactivity under specific conditions. The compound’s ability to participate in further chemical reactions, such as nucleophilic substitution, is valuable in these contexts.

3,5-Dinitrobenzoic acid also has relevance in the study of environmental and chemical processes. Due to the presence of nitro groups, the compound is of interest in research concerning the behavior of nitroaromatic compounds in the environment, particularly in terms of their potential for pollution or biodegradation. Nitrobenzoic acids have been examined in the context of their environmental impact, as they are used in the manufacture of explosives and other industrial products, leading to the study of their persistence and toxicity in the environment.

The compound has also been studied for its potential applications in the pharmaceutical industry. Nitrobenzoic acids and their derivatives, including 3,5-dinitrobenzoic acid, have been investigated for their bioactive properties, although 3,5-dinitrobenzoic acid itself has not been widely marketed as a drug. Nonetheless, its derivatives and related compounds are of interest for their potential therapeutic applications, particularly in areas like antimicrobial and anticancer drug development.

Overall, 3,5-dinitrobenzoic acid plays an important role in synthetic chemistry and industrial applications, particularly as a chemical intermediate in the production of dyes, explosives, and pharmaceuticals. Its utility in organic synthesis and materials science makes it an important compound for researchers and manufacturers in various fields.

References

Villalonga, A., López-López, D., García-Díez, E. et al. (2024). Electrochemical sensor for glutathione reductase based on screen-printed electrodes coated with 3,5-dinitrobenzoic acid-modified carbon nanotubes. Microchimica Acta, 191, 642.
DOI: https://doi.org/10.1007/s00604-024- 06728-z

Smith, G. and Wermuth, U. D. (2009). 4-(2-Hydroxyethyl)anilinium 3,5- dinitrobenzoate. Acta Crystallographica Section E: Structure Reports Online, E65, o2109.
DOI: https://doi.org/10.1107/S1600536809030426

Davey, R. J. and Jones, H. P. (2008). The crystallisation and stability of a polymorphic salt, ethylene diammonium dinitrobenzoate. New Journal of Chemistry, 32, 1686-1692.
DOI: https://doi.org/10.1039/b803583k