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

General Description

5-nitronaphthalene-1-sulphonic acid, also known as 5-NA-1-SA, is a chemical compound composed of a naphthalene ring with a nitro group and a sulfonic acid group attached at the 1-position. It is used as an intermediate in the synthesis of various organic compounds, including dyes, pigments, and pharmaceuticals. 5-NA-1-SA is water-soluble and has been employed in analytical chemistry as a reagent for the detection and quantification of ammonia and amines. It is also a potential precursor for the production of corrosion inhibitors and agricultural chemicals. The compound has been the subject of research into its environmental fate and potential toxicological effects due to its presence in industrial effluents and wastewaters.

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

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

Downstream Products

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

Relevant articles and documents

Preparation method of 1-naphthylamine-5-sulfonic acid

The invention discloses a preparation method of 1-naphthylamine-5-sulfonic acid. The preparation method comprises the following steps of step one, sulfonation: refined naphthalene is added after sulfuric acid is added to a sulfonation pot and stirred, steam is turned on for warming, and the reaction is kept for a period of time; then second batch of sulfuric acid is added, and the reaction is kept for a period of time; step two, nitrification: nitric acid is added, the temperature is controlled, and the reaction is kept for a period of time; the acidity is enabled to reach 45%-46%, and the amino value is larger than or equal to 410 g/kg; step three, neutralization: dolomite suspension liquid is added, excess sulfuric acid and hydrogen ions on the sulfonic acid group are neutralized, and the end point is reached if the color of congo red test paper doesn't change into blue; step four, reduction: iron powder is added, the reduction rate is controlled to be above 99%, and the amino value is controlled to be between 90 g/t to 110 g/t; step five, acidification: 1-naphthylamine-8-sulfonic acid is subjected to acidification separation to prepare 1-naphthylamine-5-sulfonic acid mother liquor; step six, the 1-naphthylamine-5-sulfonic acid mother liquor is acidized to further prepare the 1-naphthylamine-5-sulfonic acid.

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.