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HomeProduct name list1-Amino-2-naphthol-4-sulfonic acid

1-Amino-2-naphthol-4-sulfonic acid

Synonym(s):1-Amino-2-hydroxy-4-naphthalenesulfonic acid;1-Amino-2-naphthol-4-sulfonic acid

  • CAS NO.:116-63-2
  • Empirical Formula: C10H9NO4S
  • Molecular Weight: 239.25
  • MDL number: MFCD00004019
  • EINECS: 204-147-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-11-06 14:44:11
1-Amino-2-naphthol-4-sulfonic acid Structural

What is 1-Amino-2-naphthol-4-sulfonic acid?

Chemical properties

1-Amino-2-hydroxynaphthalene-4-sulfonic acid [116-63-2]. (4-amino-3-hydroxynaphthalene-1-sulfonic acid), B€oniger acid, C10H9NO4S, Mr 239.2, is obtained as white or gray needles of the hemihydrate, which is only sparingly soluble in hot water. The alkali-metal salts are soluble in water, but the solutions slowly oxidize in air. Oxidation with nitric acid gives 1,2- naphthoquinone-4-sulfonic acid.

The Uses of 1-Amino-2-naphthol-4-sulfonic acid

1-Amino-2-naphthol-4-sulfonic acid can be used in determination of phosphate.

The Uses of 1-Amino-2-naphthol-4-sulfonic acid

4-Amino-3-hydroxy-1-naphthalenesulfonic acid is used as mordant dyes and acid dyes intermediate.

Definition

ChEBI: 4-amino-3-hydroxynaphthalene-1-sulfonic acid is a naphthalenesulfonic acid and an aminonaphthalene. It has a role as a mutagen. It is functionally related to a 2-naphthol.

Production Methods

2-Naphthol is dissolved in dilute aqueous sodium hydroxide and precipitated in finely divided form by addition of sulfuric acid at 5℃. Sodium nitrite solution is added to the slightly alkaline suspension, followed by sulfuric acid to effectthe nitrosation while the temperature is held at 5 – 8℃. The suspension of 1-nitroso2-naphthol is neutralized with aqueous sodium hydroxide; a solution of sodium bisulfite is then added. The temperature is allowed to rise to 20℃, and the soluble bisulfite addition complex is formed. Excess sulfuric acid is then added and the temperature is raised to 40℃, whereupon reductive rearrangement takes place and the product slowly crystallizes at 50℃. Filtration and washing give the product as a 25 % paste in 80 % yield. All plant items and reactants must be free from iron to avoid complex formation.

Purification Methods

Purify it by warming 15g of the acid, 150g of NaHSO3 and 5g of Na2SO3(anhydrous) with 1L of water to ca 90o, shaking until most of the solid had dissolved, then filtering hot. The precipitate obtained by adding 10mL of conc HCl to the cooled filtrate is collected, washed with 95% EtOH until the washings are colourless, and is dried under vacuum over CaCl2. It is stored in a dark-coloured bottle, in the cold [Chanley et al. J Am Chem Soc 74 4347 1952]. [Beilstein 14 IV 2825.]

Properties of 1-Amino-2-naphthol-4-sulfonic acid

Melting point: 290 °C (dec.)(lit.)
Density  1.4338 (rough estimate)
refractive index  1.6500 (estimate)
storage temp.  Store below +30°C.
solubility  DMSO (Slightly), Methanol (Slightly)
pka -0.49±0.40(Predicted)
form  Powder
color  White to light pink
Water Solubility  insoluble
Merck  14,454
BRN  2697469
Stability: Stable. Incompatible with strong bases, acid chlorides, acid anhydrides, strong oxidizing agents.
CAS DataBase Reference 116-63-2(CAS DataBase Reference)
NIST Chemistry Reference 1-Naphthalenesulfonic acid,4-amino-3-hydroxy-(116-63-2)
EPA Substance Registry System 1-Naphthalenesulfonic acid, 4-amino-3-hydroxy- (116-63-2)

Safety information for 1-Amino-2-naphthol-4-sulfonic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 1-Amino-2-naphthol-4-sulfonic acid

InChIKey RXCMFQDTWCCLBL-UHFFFAOYSA-N

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