1-Naphthylamine-4-sulfonic Acid
Title: 1-Naphthylamine-4-sulfonic Acid
CAS Registry Number: 84-86-6
CAS Name: 4-Amino-1-naphthalenesulfonic acid
Additional Names: naphthionic acid; Piria's acid
Molecular Formula: C10H9NO3S
Molecular Weight: 223.25
Percent Composition: C 53.80%, H 4.06%, N 6.27%, O 21.50%, S 14.36%
Literature References: Prepd on a large-scale by heating a-naphthylamine with equimolar amounts of concd H2SO4 at 180-200° or by heating a-naphthylamine acid sulfate: Fierz-David, Blangey, Fundamental Processes of Dye Chemistry (Interscience, New York, 1949).
 
Derivative Type: Sesquihydrate
Properties: Shiny needles from water. d425 1.673. Dec on heating without melting (the amide mp 206°). K at 25° = 2.1´10-3. One gram dissolves in 3.45 l of water at 10°, in 3.22 l at 20°, in 1.69 l at 50°, in 438.5 ml at 100°. Very sparingly sol in alcohol, ether. Practically insol in acetic acid and acetic anhydride, but becomes sol when some pyridine is added. Sol in dil solns of alkali hydroxides or carbonates with a blue fluorescence.
Melting point: Dec on heating without melting (the amide mp 206°)
Density: d425 1.673
 
Derivative Type: Sodium salt tetrahydrate
Additional Names: Naphthionine
Manufacturers' Codes: 101-E
Molecular Formula: C10H8NNaO3S.4H2O
Molecular Weight: 317.29
Percent Composition: C 37.85%, H 5.08%, N 4.41%, Na 7.25%, O 35.30%, S 10.11%
Literature References: Ref: Piria, Ann. 78, 41 (1851).
Properties: Large monoclinic prisms from water, loses 3½ mols water at 80°, anhydr at 130°. Sweet aftertaste. Freely sol in water with a blue fluorescence. Also sol in 95% alc. Practically insol in ether. Sparingly sol in concd aq and alcoholic caustic solns. pH of a 1% aq soln 6.8. Even ampuled aq solns discolor under the influence of light.
 
Derivative Type: Sodium salt glucoside
Additional Names: Naphthionine N-glucoside
Manufacturers' Codes: 101-G
Molecular Formula: C16H20NNaO8S
Molecular Weight: 409.39
Percent Composition: C 46.94%, H 4.92%, N 3.42%, Na 5.62%, O 31.26%, S 7.83%
Literature References: Ref: Estève et al., Ann. Pharm. Fr. 10, 680 (1952).
Properties: White powder, bitter taste. Dec 255°. [a]D23.5 -113° (c = 10). Sol in water; slightly sol in alcohol. Practically insol in ether.
Optical Rotation: [a]D23.5 -113° (c = 10)
 
Use: The sodium salt is an important dye intermediate in the manuf of Congo Red, Fast Red A, Azo Rubine, and similar azo dyes.
Therap-Cat: Sodium salt as hemostatic.
Keywords: Hemostatic.

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