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2-Amino-5-nitrobenzenesulfonic acid
[CAS# 96-75-3]

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Identification
ClassificationOrganic raw materials >> Amino compound >> Sulfonic acid amino compound
Name2-Amino-5-nitrobenzenesulfonic acid
Synonymsp-Nitroaniline-o-sulfonic acid
Molecular StructureCAS # 96-75-3, 2-Amino-5-nitrobenzenesulfonic acid
Molecular FormulaC6H6N2O5S
Molecular Weight218.19
CAS Registry Number96-75-3
EC Number202-531-5
SMILESC1=CC(=C(C=C1[N+](=O)[O-])S(=O)(=O)O)N
Properties
Density1.7±0.1 g/cm3, Calc.*
Index of Refraction1.662, Calc.*
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol   GHS07 Warning  Details
Risk StatementsH319  Details
Safety StatementsP264+P265-P280-P305+P351+P338-P337+P317  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Skin irritationSkin Irrit.2H315
SDSAvailable
up Discovery and Applications
2-Amino-5-nitrobenzenesulfonic acid is an aromatic sulfonic acid derivative characterized by the presence of an amino group and a nitro group attached to a benzene ring. This compound has the molecular formula C6H6N2O4S and is often used as an intermediate in the synthesis of various chemical products, particularly in the dye and pigment industries. It plays a significant role in the development of organic compounds used in textile and other industries, where its chemical reactivity and functional groups are exploited for creating a range of synthetic dyes.

The discovery of aromatic sulfonic acids dates back to the 19th century, with early studies on the sulfonation of aromatic compounds leading to the synthesis of sulfonic acids as intermediates for dyes, pharmaceuticals, and other applications. The specific compound 2-amino-5-nitrobenzenesulfonic acid is derived from the functionalization of benzene, a process which has been explored in-depth since the industrialization of organic chemistry. The introduction of both an amino group and a nitro group to the aromatic ring, along with the sulfonic acid moiety, gave this compound unique properties, making it highly useful in industrial applications.

2-Amino-5-nitrobenzenesulfonic acid finds its primary application in the manufacture of dyes, particularly azo dyes. The sulfonic acid group facilitates the solubility of the dye in water, making it an essential component in dyeing processes, especially in the textile and leather industries. Azo compounds, which are synthesized from such intermediates, are widely used in the production of vibrant colors for clothing, cosmetics, and home goods. The presence of both the amino and nitro groups in 2-amino-5-nitrobenzenesulfonic acid makes it a versatile precursor for the synthesis of various colored compounds with different functional properties, including stability and intensity.

In addition to its role in the dye industry, 2-amino-5-nitrobenzenesulfonic acid has applications in the field of analytical chemistry. It can be used as a reagent in certain types of chemical analyses, such as the detection of metals and other compounds through complexation reactions. Its ability to form coordination complexes with metal ions makes it valuable for use in analytical techniques where metal content needs to be determined, particularly in water and soil samples.

Moreover, 2-amino-5-nitrobenzenesulfonic acid has been studied for its potential biological activity. While it is not widely used in medicinal chemistry, compounds with similar structures have demonstrated antimicrobial and antitumor properties, sparking interest in exploring the biological effects of this and similar sulfonic acid derivatives. Research is ongoing to evaluate its toxicity and any potential therapeutic applications in pharmaceutical development.

In summary, 2-amino-5-nitrobenzenesulfonic acid is an important industrial chemical with applications in the synthesis of dyes, as well as potential uses in analytical chemistry. Its discovery and development have significantly contributed to the growth of the dye industry and continue to play a role in the creation of new materials for commercial and industrial use.

References

2007. Sensing elements of optical sensors based on polystyrene with covalently immobilized reagents. Journal of Analytical Chemistry, 62(3).
DOI: 10.1134/s1061934807030148

2006. New metallochromic indicator for barium: Determination of sulfate in water and soil extracts. Journal of Analytical Chemistry, 61(12).
DOI: 10.1134/s1061934806120057

2003. Effect of Substituent in Diazotized Orthanilic Acid on the Azo Coupling with 7-Acetylamino-4-hydroxynaphthalene-2-sulfonic Acid in Citrate-Phosphate Buffers. Russian Journal of General Chemistry, 73(7).
DOI: 10.1023/b:rugc.0000007618.08375.43
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