17521-00-5

Basic information

• Product Name: 5-nitronaphthalene-1-sulphonic acid
• Synonyms: 5-nitronaphthalene-1-sulphonic acid;1-Nitro-5-naphthalenesulfonic acid;5-Nitro-1-naphthalenesulfonic acid
• CAS NO: 17521-00-5
• Molecular Formula: C₁₀H₇NO₅S
• Molecular Weight: 253.23128
• EINECS: 241-518-9
• Mol File: 17521-00-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.601g/cm³
• Refractive Index: 1.693
• CAS DataBase Reference: 5-nitronaphthalene-1-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitronaphthalene-1-sulphonic acid(17521-00-5)
• EPA Substance Registry System: 5-nitronaphthalene-1-sulphonic acid(17521-00-5)

Safety Data

• Hazardous Substances Data: 17521-00-5(Hazardous Substances Data)

Usage

Description

5-nitronaphthalene-1-sulphonic acid, also known as 5-NA-1-SA, is a chemical compound that features a naphthalene ring with a nitro group and a sulfonic acid group attached at the 1-position. It is recognized for its water solubility and serves as an intermediate in the synthesis of a variety of organic compounds, such as dyes, pigments, and pharmaceuticals.

Uses

Used in Organic Synthesis:
5-nitronaphthalene-1-sulphonic acid is used as an intermediate for the synthesis of various organic compounds, including dyes and pigments, due to its reactive functional groups that facilitate chemical reactions.
Used in Pharmaceutical Production:
As a pharmaceutical intermediate, 5-nitronaphthalene-1-sulphonic acid is utilized in the development and manufacturing of different medicinal agents, contributing to the creation of new drugs.
Used in Analytical Chemistry:
5-nitronaphthalene-1-sulphonic acid is used as a reagent for the detection and quantification of ammonia and amines, given its water solubility and chemical properties that allow for specific analytical reactions.
Used in Corrosion Inhibition:
It serves as a potential precursor for the production of corrosion inhibitors, which are essential in protecting materials from degradation in various industrial applications.
Used in Agricultural Chemicals:
5-nitronaphthalene-1-sulphonic acid is also a precursor in the production of agricultural chemicals, playing a role in the development of products that contribute to crop protection and enhancement.
Environmental and Toxicological Research:
5-nitronaphthalene-1-sulphonic acid is a subject of research into its environmental fate and potential toxicological effects, particularly in relation to its presence in industrial effluents and wastewaters, which is crucial for understanding its impact on ecosystems and human health.

InChI:InChI=1/C10H7NO5S/c12-11(13)9-5-1-4-8-7(9)3-2-6-10(8)17(14,15)16/h1-6H,(H,14,15,16)

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 85-47-2 1-naphthalenesulfonic acid 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 91-20-3 naphthalene 

Downstream Products

• 84-89-9 1-aminonaphthalene-5-sulfonic acid 
• 7664-93-9 sulfuric acid 
• 134-32-7 1-amino-naphthalene 

Relevant articles and documents

Method for hydrogen catalyzed preparation of 1-naphthylamine-8-sulfonic acid

The invention discloses a method for hydrogen catalyzed preparation of 1-naphthylamine-8-sulfonic acid. The method includes the reduction steps of: placing a solution containing 1-sulfonyl-8-nitronaphthalene in a reduction pot, adding nickel powder, conducting starting and stirring, enclosing the reduction pot and pumping vacuum, then introducing hydrogen and maintaining the pressure at 1.2-1.3MPa, heating the mixed liquid to a temperature of 100-110DEG C, pumping out the mixed liquid from the bottom continuously and letting it flow into the reduction pot from the top, at the same time pumping out the gas from the top continuously and blowing the gas into the reduction pot from the bottom. The method for hydrogen catalyzed preparation of 1-naphthylamine-8-sulfonic acid provided by the invention can prepare the 1-naphthylamine-8-sulfonic acid product meeting the market requirements, and also can overcome the disadvantages of existing iron powder catalyzed preparation methods.

The positional reactivity order in the sulfur trioxide sulfonation of benzene and naphtalene derivatives containing an electron-withdrawing substituent

The reaction of sulfur trioxide with derivatives of benzene and naphthalene containing an electron-withdrawing substituent, viz.-SO3H, -SO2Ph, -NO2, -CHO, -COPh, -CO2H, and -CO2Me, in dichloromethane as solvent at ca. 22 deg C has been studied by analysis of the resulting mixtures of the sulfo derivatives with 1H-NMR.The initial sulfonation of the benzene derivatives yields the corresponding 3-sulfonic acid (3-S) and subsequently, with the exception of nitrobenzene and methyl benzoate, small amounts of 3,5-S2.Benzenesulfonic acid in addition undergoes sulfonylation giving 3,3'-di- and 3,5,3'-trisulfodiphenyl sulfone.Monosulfonation of naphtalene-1-S yields the 1,5-S2, 1,6-S2 and 1,7-S2 derivatives in a ratio of 71:20:9.On using a large excess of SO3, the eventual products are 1,3,5-S3, 1,3,6-S3 and 1,3,5,7-S4.Monosulfonation of naphthalene yields 5-S, 6-S, 7-S and 8-S in a 55:9:6:30 ratio, that of 1-benzoylnaphthalene 5-S, 6-S and 7-S in a ratio of 83:11:6, and 1-nitronaphtalene only the 5-S.The absence of peri sulfonation with 1-sulfo-, 1-benzoyl- and 1-nitronaphthalene is due to prohibitive steric hidrance. 1-Naphthoic acid and its methyl ester upon SO3 sulfonation and aqueous work-up both yield 5- and 8-sulfonaphthoic acid in a ratio of 65:35 and 77:21, respectively.The initially formed peri-substituted product is the intramolecular anhydride of 8-sulfo-1-naphthoic acid (5).All the 2-substituted naphthalenes yield 5-S and 8-S upon SO3 sulfonation of which the former sulfo isomer is far in excess.The positional reactivity orders for the SO3 sulfonation of the monosubstituted naphthalene derivatives are discussed in terms of the difference in reactivity of the α- and β-positions, and the steric and electronic effects of the deactivating substituent.

Process for the production of nitro derivatives of aromatic compounds

Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.