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HomeProduct name listNaphthionic acid

Naphthionic acid

Synonym(s):1-Naphthylamine-4-sulfonic acid;Naphthionic acid

  • CAS NO.:84-86-6
  • Empirical Formula: C10H9NO3S
  • Molecular Weight: 223.25
  • MDL number: MFCD00004027
  • EINECS: 201-567-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-15 19:00:21
Naphthionic acid Structural

What is Naphthionic acid?

Chemical properties

?slightly greyish to beige powder and granules. 1-Aminonaphthalene- 4 -sulfonic acid [84- 86-6]. (4-aminonaphthalene-1-sulfonic acid), naphthionic acid, Piria’s acid, C10H9NO3S, Mr 223.24, is sparingly soluble in water (0.25 % at 100℃), but the sodium, potassium, calcium, and barium salts are all readily soluble. Chlorination of 1-Aminonaphthalene- 4 -sulfonic acid with copper(II) chloride produces 4-chloro-1-aminonaphthalene, whereas the action of chlorine on an aqueous sulfuric acid solution gives 2,3-dichloro-1,4-naphthoquinone. High-temperature bromination gives 2,4- dibromo-1-aminonaphthalene, whereas vigorous nitration yields 2,4-dinitro-1-hydroxynaphthalene. Sulfonation with 25 % oleum gives 1-aminonaphthalene-4,6- and 4,7-disulfonic acids, whereas prolonged heating with sulfuric acid at 130℃ leads to 1-aminonaphthalene-5- and 6- sulfonic acids. Hydrolysis of the 1-amino group to give 1-hydroxynaphthalene-4-sulfonic acid is best achieved by a reverse-Bucherer reaction but also results from prolonged heating with 50 % sodium hydroxide.

The Uses of Naphthionic acid

Intermediate for azo dyes, e.g., Congo red.

The Uses of Naphthionic acid

4-Amino-1-naphthalenesulfonic acid has potent therapeutic applications. Its sodium salt has been used as non-toxic hemostatic. It is also a metabolite of azo dyes.

Definition

ChEBI: Naphthionic acid is an aminonaphthalenesulfonic acid.

Production Methods

Naphthionic acid was first prepared by PIRIA by heating 1-nitronaphthalene with ammonium sulfite; however, the formation of 1-aminonaphthalene-2,4-disulfonic acid and other byproducts makes this route unattractive for large-scale production. Although it can also be prepared by direct sulfonation of 1-naphthylamine, it is more conveniently produced by a solvent-bake process. 1-Naphthylamine is dissolved in o-dichlorobenzene and H2SO4 (molar ratio 1 : 1) added to form a suspension of the sulfate. After being heated gradually to 180℃, the reaction is completed by maintaining this temperature until all the water of reaction has been distilled off with solvent recycle. The product is extracted from the final mixture by addition to aqueous sodium carbonate solution. After separation, the aqueous layer is steam distilled to remove residual solvent, and the product is salted out, filtered, and washed with brine to give sodium naphthionate as a paste in 90 % yield.

General Description

4-Amino-1-naphthalenesulfonic acid is a diazo compound. It is also known as Piria′s acid.

Purification Methods

It crystallises from H2O as needles of the 0.5 hydrate. Salt solutions fluoresce strongly blue. The S-benzylisothiuronium salt has m 195o (from aqueous EtOH). [Beilstein 14 IV 2793.]

Properties of Naphthionic acid

Melting point: ≥300 °C(lit.)
Boiling point: 220°C (rough estimate)
Density  1.67
refractive index  1.5250 (estimate)
storage temp.  Store below +30°C.
solubility  Sparingly soluble in dichloromethane. Soluble in aqueous base.
form  powder to crystal
pka pK1: 2.81 (25°C)
color  White to Light yellow to Light red
Water Solubility  309.9mg/L(20 ºC)
Merck  14,6403
BRN  1971299
CAS DataBase Reference 84-86-6(CAS DataBase Reference)
NIST Chemistry Reference 4-Amino-1-naphthalene sulfonic acid(84-86-6)
EPA Substance Registry System 4-Amino-1-naphthalenesulfonic acid (84-86-6)

Safety information for Naphthionic acid

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Naphthionic acid

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