2-Aminonaphthalene-1-sulfonic acid
Synonym(s):2-Naphthylamine-1-sulfonic acid;Tobias acid
- CAS NO.:81-16-3
- Empirical Formula: C10H9NO3S
- Molecular Weight: 223.25
- MDL number: MFCD00003988
- EINECS: 201-331-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-24 19:19:26
What is 2-Aminonaphthalene-1-sulfonic acid?
Chemical properties
Grey white to light pink powder. 2-Aminonaphthalene-1-sulfonic acid [81-16-3]. Tobias acid, C10H9NO3S, Mr 223.24, is sparingly soluble in water but the sodium salt is readily soluble. Coupling with diazo compounds takes place in the 1-position with elimination of the sulfonic acid group.
The Uses of 2-Aminonaphthalene-1-sulfonic acid
Azo dye intermediate, optical brighteners.
The Uses of 2-Aminonaphthalene-1-sulfonic acid
2-Amino-1-naphthalenesulfonic acid has been used in the preparation of 2-(2-naphthylamino)benzoxazole by reacting with 2-chlorobenzoxazole.
Production Methods
2-Hydroxynaphthalene-1-sulfonic acid is heated with a mixture of ammonia and ammonium sulfite in an autoclave at 150 ℃ and 1 MPa for 30 h. The reaction mixture is added to a slurry of lime, and excess ammonia is driven off. Inorganic calcium salts are filtered off at 80℃, and the filtrate is acidified with hydrochloric acid at 40℃ to precipitate Tobias acid in 95 % yield. Care must be taken throughout the process to avoid desulfonation and formation of 2- naphthylamine.
General Description
2-Amino-1-naphthalenesulfonic acid is a manufacturing intermediate in the monosulfo monoazo color additive D&C Red No. 34 and its lakes.
Purification Methods
Crystallise the acid under nitrogen from boiling water and dry it in a steam oven [Bryson Trans Faraday Soc 47 522, 527 1951]. [Beilstein 14 III 2240, 14 IV 2792.]
Properties of 2-Aminonaphthalene-1-sulfonic acid
Melting point: | 180 °C |
Boiling point: | 220°C (rough estimate) |
Density | 1.3588 (rough estimate) |
refractive index | 1.5250 (estimate) |
storage temp. | -20°C Freezer, Under inert atmosphere |
solubility | DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly, Heated) |
pka | pK1: 2.35 (25°C) |
form | Solid |
color | White to Off-White |
Water Solubility | 4.083g/L(20 ºC) |
Merck | 14,6406 |
BRN | 613084 |
CAS DataBase Reference | 81-16-3(CAS DataBase Reference) |
NIST Chemistry Reference | 2-Naphthylamine-1-sulfonic acid(81-16-3) |
EPA Substance Registry System | 2-Amino-1-naphthalenesulfonic acid (81-16-3) |
Safety information for 2-Aminonaphthalene-1-sulfonic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation H320:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 2-Aminonaphthalene-1-sulfonic acid
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