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

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

Product Name:
1-Amino-2-naphthol-4-sulfonic acid
Synonyms:
  • 4-Amino-3-hydroxy-1-naphthalenesulfonic acid, ACS, 98+%
  • 1-AMINO-2-NAPHTH-4-SULFONIC AC
  • 1-amino-2-naphthol-4-sulfonic acid test solution(ChP)
  • 1-AMINO-2-NAPHTHOL-4-SULPHONIC ACID extrapure AR
  • 3-Hydroxynaphthionic acid
  • 4-Amino-3-hydroxy-1-naphthalenesulfonic acid,95%
  • 4-amino-3-hydroxy-1-Naphthalenesulfonic acid 1-amino-2-naphthol-4-sulfonic acid 4-Amino-3-hydroxynaphthalene-1-sulfonic acid
  • 4-Amino-3-hydroxy-1-naphthalenesulfonic acid,1-Amino-2-naphthol-4-sulfonic acid
CAS:
116-63-2
MF:
C10H9NO4S
MW:
239.25
EINECS:
204-147-3
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Intermediates of Dyes and Pigments
  • Organic Building Blocks
  • Sulfonic/Sulfinic Acids
  • Sulfur Compounds
  • Sulphur Derivatives
  • Organic acids
Mol File:
116-63-2.mol
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1-Amino-2-naphthol-4-sulfonic acid Chemical Properties

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.
InChIKey
RXCMFQDTWCCLBL-UHFFFAOYSA-N
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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
37/39-26
RIDADR 
3265
WGK Germany 
3
RTECS 
QK1292000
TSCA 
Yes
HazardClass 
IRRITANT
PackingGroup 
III
HS Code 
29222100

MSDS

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1-Amino-2-naphthol-4-sulfonic acid Usage And Synthesis

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.

Uses

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

Uses

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

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.]

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