35400-55-6

Basic information

• Product Name: 5-amino-4-hydroxynaphthalene-2-sulphonic acid
• Synonyms: 5-amino-4-hydroxynaphthalene-2-sulphonic acid;5-Amino-4-hydroxy-2-naphthalenesulfonic acid
• CAS NO: 35400-55-6
• Molecular Formula: C₁₀H₉NO₄S
• Molecular Weight: 239.24776
• EINECS: 252-546-6
• Mol File: 35400-55-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.627g/cm³
• Refractive Index: 1.748
• CAS DataBase Reference: 5-amino-4-hydroxynaphthalene-2-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-4-hydroxynaphthalene-2-sulphonic acid(35400-55-6)
• EPA Substance Registry System: 5-amino-4-hydroxynaphthalene-2-sulphonic acid(35400-55-6)

Safety Data

• Hazardous Substances Data: 35400-55-6(Hazardous Substances Data)

Usage

General Description

5-amino-4-hydroxynaphthalene-2-sulphonic acid is a chemical compound with the molecular formula C10H9NO4S. It is a derivative of naphthalene and contains an amino group and a sulphonic acid group. 5-amino-4-hydroxynaphthalene-2-sulphonic acid is commonly used in the production of dyes and pigments due to its ability to produce bright and vivid colors. It is also used as a pH indicator in chemical laboratories and as a fluorescent dye in biological studies. Additionally, 5-amino-4-hydroxynaphthalene-2-sulphonic acid is used in the manufacturing of pharmaceuticals and as an intermediate for organic synthesis.

InChI:InChI=1/C10H9NO4S/c11-8-3-1-2-6-4-7(16(13,14)15)5-9(12)10(6)8/h1-5,12H,11H2,(H,13,14,15)

Synthetic route

4,5-diamino-naphthalene-2-sulfonic acid (457629-68-4) → 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6)

Conditions	Yield
With sulfuric acid at 120℃;

sulfuric acid (7664-93-9) + 4,5-diamino-naphthalene-2-sulfonic acid (457629-68-4) → 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6)

Conditions	Yield
at 120℃; im geschlossenen Gefaess;
at 120℃; im geschlossenen Gefaess;

acidic sodium salt of/the/ 8-amino-naphthol-(1)-disulfonic acid-(3.5) → 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6)

Conditions	Yield
With water; zinc

acidic sodium salt of/the/ naphthylamine-(1)-disulfonic acid-(6.8) → 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6)

Conditions	Yield
With potassium hydroxide at 180 - 200℃;

8-Aminonaphthalene-1,3-disulfonic acid (41131-26-4) + KOH-solution → 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6)

Conditions	Yield
at 180 - 200℃;

2,6-diamino-9,10-anthraquinone (131-14-6) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C34H20N6O10S2(2-)*2Na(1+)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 20 - 40℃; for 0.666667h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid at 5 - 10℃; pH=0.5 - 1;	90%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 40℃; for 0.5h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide at 5 - 10℃; pH=0.5 - 1;

2,6-diamino-9,10-anthraquinone (131-14-6) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C34H20N6O10S2(2-)*2Na(1+)

Conditions	Yield
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 20 - 40℃; for 0.666667h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid at 0 - 5℃; pH=8 - 9;	80%
Stage #1: 2,6-diamino-9,10-anthraquinone With sulfuric acid at 40℃; for 0.5h; Stage #2: With nitrosylsulfuric acid at 20 - 25℃; for 4h; Stage #3: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide at 0 - 5℃; pH=8 - 9;

amino-benzene-1,4-disulfonic acid (98-44-2) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C16H13N3O10S3 (1458587-10-4)

Conditions	Yield
Stage #1: amino-benzene-1,4-disulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; Stage #2: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide In water at 0 - 20℃; for 3.5h; pH=0.8 - 1.1;	70%
Stage #1: amino-benzene-1,4-disulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; Stage #2: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium hydroxide at 0 - 20℃; for 3.5h; pH=0.8 - 1.1;

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 5,6-diamino-4-hydroxynaphthalene-2-sulfonic acid

Conditions	Yield
Stage #1: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium carbonate; sodium nitrite; 4-aminobenzene sulfonic acid; hydrogenchloride In water at 5 - 20℃; Stage #2: With sodium pyrosulfate at 50℃; for 4h; Further stages.;	45%

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 8-hydroxy-6-sulfo-naphthalene-1-diazonium-betaine

Conditions	Yield
With cis-nitrous acid

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 9-hydroxy-2-(1-hydroxy-naphthalen-2-yl)-3H-naphtho[1,2-d]imidazole-7-sulfonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-aminobenzenesulfonic acid; NaNO2; Na2CO3 / HCl / H2O / 5 - 20 °C 1.2: 45 percent / Na2S2O7 / 4 h / 50 °C 2.1: NaHSO3 / H2O; ethanol / Heating View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 9-hydroxy-2-(2-hydroxy-naphthalen-1-yl)-3H-naphtho[1,2-d]imidazole-7-sulfonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-aminobenzenesulfonic acid; NaNO2; Na2CO3 / HCl / H2O / 5 - 20 °C 1.2: 45 percent / Na2S2O7 / 4 h / 50 °C 2.1: 75 percent / sodium bisulfite / ethanol; H2O / 1 h / Heating View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 9-hydroxy-2-(2-hydroxy-3',4'-dimethyl-biphenyl-3-yl)-3H-naphtho[1,2-d]imidazole-7-sulfonic acid; hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-aminobenzenesulfonic acid; NaNO2; Na2CO3 / HCl / H2O / 5 - 20 °C 1.2: 45 percent / Na2S2O7 / 4 h / 50 °C 2.1: NaHSO3 / ethanol; H2O / Heating View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C22H17N3O12S4 (1458587-11-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / water / 2 h / 20 °C / pH 11 - 12 View Scheme
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / 2 h / 20 °C / pH 11 - 12 View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C46H24N10O22S6(6-)*6Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sulfuric acid / 0.5 h / 40 °C 2.2: 4 h / 20 - 25 °C 2.3: 0 - 5 °C / pH 8 - 9 View Scheme
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sulfuric acid / 0.67 h / 20 - 40 °C 2.2: 4 h / 20 - 25 °C 2.3: 0 - 5 °C / pH 8 - 9 View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C32H18N5O19S6(5-)*5Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / water / 2 h / 20 °C / pH 11 - 12 3.1: hydrogenchloride; sodium nitrite / water / 2 h / 0 °C 3.2: 5 h / 0 - 5 °C / pH 1.5 View Scheme
Multi-step reaction with 3 steps 1.1: sodium nitrite; hydrogenchloride / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / 2 h / 20 °C / pH 11 - 12 3.1: sodium nitrite; hydrogenchloride / water / 2 h / 0 °C 3.2: 5 h / 0 - 5 °C / pH 1.5 View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C38H20N8O24S7(6-)*6Na(1+)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; sodium nitrite / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / water / 2 h / 20 °C / pH 11 - 12 3.1: hydrogenchloride; sodium nitrite / water / 2 h / 0 °C 3.2: 5 h / 0 - 5 °C / pH 1.5 4.1: sodium hydroxide / water / 1 h / 40 °C / pH 5 - 6 View Scheme

C16H11NO9S3(2-)*2Na(1+) + 5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C30H16N5O18S5(5-)*5Na(1+)

Conditions	Yield
Stage #1: C16H11NO9S3(2-)*2Na(1+) With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 5℃; Stage #2: 5-amino-4-hydroxy-2-naphthalenesulphonic acid In water at 0 - 5℃; pH=0.8 - 1; Further stages;
Stage #1: C16H11NO9S3(2-)*2Na(1+) With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 5℃; Stage #2: 5-amino-4-hydroxy-2-naphthalenesulphonic acid With sodium acetate In water at 0 - 5℃; for 0.5h; pH=0.8 - 1; Further stages;

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → 6Na(1+)*C32H16N8O22S6(6-)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / 2 h / 20 °C / pH 11 - 12 3.1: sodium nitrite; hydrogenchloride / water / 2 h / 0 °C 3.2: 5 h / 0 - 5 °C / pH 1.5 4.1: sodium nitrite; hydrogenchloride / water / 5 °C 4.2: 1 h / 40 °C / pH 5 - 12 View Scheme

5-amino-4-hydroxy-2-naphthalenesulphonic acid (35400-55-6) → C38H20N8O24S7(6-)*6Na(1+)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / water / 5 °C 1.2: 3.5 h / 0 - 20 °C / pH 0.8 - 1.1 2.1: sodium hydroxide / 2 h / 20 °C / pH 11 - 12 3.1: sodium nitrite; hydrogenchloride / water / 2 h / 0 °C 3.2: 5 h / 0 - 5 °C / pH 1.5 4.1: sodium nitrite; hydrogenchloride / water / 5 °C 4.2: 1 h / 0 - 5 °C / pH 8.5 - 9.5 View Scheme

Upstream product

• 41131-26-4 8-Aminonaphthalene-1,3-disulfonic acid 
• 7664-93-9 sulfuric acid 
• 457629-68-4 4,5-diamino-naphthalene-2-sulfonic acid 

Downstream Products

• 1458587-11-5 C₂₂H₁₇N₃O₁₂S₄ 
• 1458587-10-4 C₁₆H₁₃N₃O₁₀S₃ 

Relevant articles and documents

Copper complexes of sulpho groups containing disazo dyestuffs

The new disazo dyestuffs of the formula (I) STR1 in which the substituents and indices have the meaning given in the description, and salts thereof are outstandingly suitable for dyeing cellulose-containing materials and leather in blue shades having good wet- and light-fastnesses.