148-25-4

Basic information

• Product Name: 1,8-Dihydroxynaphthylene-3,6-disulfonic acid
• Synonyms: 4,5-dihydroxy-7-naphthalenedisulfonicacid;7-Naphthalenedisulfonicacid,4,5-dihydroxy-2;Chrmotropicacid;4,5-DIHYDROXY-2,7-NAPHTHALENEDISULFONIC ACID;4,5-dihydroxynaphthalene-2,7-disulphonic acid;1,8-DIHYDROXYNAPHTHALENE-3,6-DISULFONIC ACID;1,8-DIHYDROXYNAPHTHYLENE-3,6-DISULFONIC ACID;CHROMOGEN
• CAS NO: 148-25-4
• Molecular Formula: C₁₀H₈O₈S₂
• Molecular Weight: 320.3
• EINECS: 205-712-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 148-25-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 429.2°C (rough estimate)
• Appearance: /
• Density: 1.7929 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.51±0.40(Predicted)
• CAS DataBase Reference: 1,8-Dihydroxynaphthylene-3,6-disulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Dihydroxynaphthylene-3,6-disulfonic acid(148-25-4)
• EPA Substance Registry System: 1,8-Dihydroxynaphthylene-3,6-disulfonic acid(148-25-4)

Safety Data

• Hazardous Substances Data: 148-25-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A naphthalenesulfonic acid that is naphthalene-2,7-disulfonic acid substituted by hydroxy groups at positions 4 and 5.

InChI:InChI=1/C10H8O8S2/c11-8-3-6(19(13,14)15)1-5-2-7(20(16,17)18)4-9(12)10(5)8/h1-4,11-12H,(H,13,14,15)(H,16,17,18)

Synthetic route

1-naphthol-3,6,8-trisulphonic acid (3316-02-7) → chromatotropic acid (148-25-4)

Conditions	Yield
With alkali hydroxide at 170 - 220℃;

4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) → chromatotropic acid (148-25-4)

Conditions	Yield
With potassium hydroxide at 260 - 280℃;
With sodium hydroxide at 260 - 280℃;
With sulfuric acid at 145℃;

1,8-diamino-3,6-naphthalenedisulfonic acid (6362-11-4) → chromatotropic acid (148-25-4)

Conditions	Yield
With diluted alkali at 260 - 280℃;
With diluted acid at 150 - 160℃;

2,2-dioxo-2λ6-naphth[1,8-cd][1,2]oxathiol-4,7-disulfonic acid + alkali hydroxides → chromatotropic acid (148-25-4)

Conditions	Yield
at 170 - 220℃; beim Verschmelzen;

8-chloro-naphthol-(1)-disulfonic acid-(3.6) → chromatotropic acid (148-25-4)

Conditions	Yield
With alkali beim Schmelzen;

naphthol-(1)-sultonedisulfonic acid → chromatotropic acid (148-25-4)

Conditions	Yield
With alkali hydroxide at 170 - 220℃;

trisodium-salt of/the/ 8-hydroxy-naphthalene-trisulfonic acid-(1,3,6)) → chromatotropic acid (148-25-4)

Conditions	Yield
With sodium hydroxide; water at 200℃;

4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + diluted alkaline solution → chromatotropic acid (148-25-4)

Conditions	Yield
at 260 - 280℃;

1-naphthol-3,6,8-trisulphonic acid (3316-02-7) + potash → chromatotropic acid (148-25-4)

Conditions	Yield
at 170 - 220℃;

1,8-diamino-3,6-naphthalenedisulfonic acid (6362-11-4) + alkaline solution → chromatotropic acid (148-25-4)

Conditions	Yield
at 260 - 280℃;

4-chloro-5-hydroxy-naphthalene-2,7-disulfonic acid (90-21-1) + alkali → chromatotropic acid (148-25-4)

Conditions	Yield
beim Verschmelzen;

1,8-diamino-3,6-naphthalenedisulfonic acid (6362-11-4) + diluted acid → chromatotropic acid (148-25-4)

Conditions	Yield
at 150 - 160℃;

3-[(2,6-dibromo-4-methylphenyl)azo]-6[(2-sulfophenyl)azo]-4,5-dihydoxynaphthalene-2,7-disulfonic acid (188641-21-6) → chromatotropic acid (148-25-4) + 3,5-dibromotoluene (1611-92-3) + benzenesulfonic acid (98-11-3)

Conditions	Yield
With potassium metaperiodate In water

3-(2,6-dibromo-4-sulfophenylazo)-6-(2-arsenophenylazo)-4,5-dihydroxynaphthalene-2,7-disulfonic acid → chromatotropic acid (148-25-4) + phenylarsonic acid (98-05-5) + 3,5-dibromobenzenesulfonic acid

Conditions	Yield
With potassium metaperiodate; bovine serum albumin In ethanol; water at 75℃; for 0.0833333h; pH=2; aq. buffer; Enzymatic reaction;

1-aminonaphthalene-3,6,8-trisulphonic acid trisodium salt → chromatotropic acid (148-25-4) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + C10H9NO7S2

Conditions	Yield
Stage #1: 1-aminonaphthalene-3,6,8-trisulphonic acid trisodium salt With sodium hydroxide In methanol at 180 - 200℃; under 21002.1 Torr; Stage #2: With sulfuric acid In methanol

naphthalene (91-20-3) → chromatotropic acid (148-25-4) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + C10H9NO7S2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfur trioxide; sulfuric acid / 65 - 150 °C 1.2: 40 °C 2.1: hydrogen / 170 °C / 150015 Torr 3.1: sodium hydroxide / methanol / 180 - 200 °C / 21002.1 Torr View Scheme

4-(4-acetylamino-2-sulphophenylazo)-2,5-di(2-acetoxyethoxy)aniline (637011-53-1) + chromatotropic acid (148-25-4) → C26H25N5O15S3 (697756-74-4)

Conditions	Yield
Stage #1: 4-(4-acetylamino-2-sulphophenylazo)-2,5-di(2-acetoxyethoxy)aniline With hydrogenchloride; aminosulfonic acid; sodium nitrite In water; acetone at 20℃; for 1h; pH=10; Stage #2: chromatotropic acid With lithium hydroxide In water; acetone at 0 - 10℃; pH=7 - 8; Stage #3: With hydrogenchloride; lithium hydroxide more than 3 stages;	67%

chromatotropic acid (148-25-4) + 4-bromo-5-nitrophthalonitrile (206268-72-6) → 9,10-dicyanobenzo[b]naphtho[1,8-ef][1,4]dioxepin-2,5-disulfonic acid

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 2h;	63.8%

chromatotropic acid (148-25-4) + 4-Dodecyl-benzenediazonium → Sodium; 6-(4-dodecyl-phenylazo)-4,5-dihydroxy-naphthalene-2-sulfonate

Conditions	Yield
pH 5;	37%

p-nitrobenzenediazonium (14368-49-1) + chromatotropic acid (148-25-4) → 3-(4-amino-phenylazo)-4,5-dihydroxy-naphthalene-2,7-disulfonic acid ; sodium salt (1681-60-3)

Conditions	Yield
With sodium sulfide

chromatotropic acid (148-25-4) + 4-ethoxybenzenediazonium (19262-82-9) → 3-(4-ethoxy-phenylazo)-4,5-dihydroxy-naphthalene-2,7-disulfonic acid

Conditions	Yield
With sodium acetate

chromatotropic acid (148-25-4) + benzene diazonium chloride (100-34-5) → 3-benzeneazo-4,5-dihydroxynaphthalene-2,7-disulfonic acid (13432-13-8)

Conditions	Yield
With sodium carbonate at 0 - 5℃;
With sodium carbonate at 0 - 5℃;

chromatotropic acid (148-25-4) + sodium ethyl sulfate (546-74-7) → 4-ethoxy-5-hydroxy-naphthalene-2,7-disulfonic acid (6837-94-1)

Conditions	Yield
With alkali at 180 - 200℃;

chromatotropic acid (148-25-4) → 4,5,7-trihydroxy-naphthalene-2-sulfonic acid

Conditions	Yield
With alkali hydroxide

chromatotropic acid (148-25-4) → 3-chloro-4,5-dihydroxy-naphthalene-2,7-disulfonic acid

Conditions	Yield
With sodium hypochlorite

chromatotropic acid (148-25-4) → 4,5-dihydroxy-3-(2-hydroxy-4-sulfo-[1]naphthylazo)-naphthalene-2,7-disulfonic acid (111796-72-6)

Conditions	Yield
With calcium hydroxide; sodium hydroxide anschliessend mit diazotierter 4-Amino-3-hydroxy-naphthalin-1-sulfonsaeure;

chromatotropic acid (148-25-4) → 3-(4-anilino-3-sulfo-phenylazo)-4,5-dihydroxy-naphthalene-2,7-disulfonic acid

Conditions	Yield
With calcium hydroxide; sodium hydroxide anschliessend mit diazotiertem 5-Amino-2-anilino-benzolsulfonsaeure in wss.Na2CO3;

chromatotropic acid (148-25-4) → 4,5-dihydroxy-6-nitroso-3-(4-sulfo-[1]naphthylazo)-naphthalene-2,7-disulfonic acid (102160-30-5)

Conditions	Yield
With hydrogenchloride; sodium nitrite anschliessend mit diazotierter 4-Amino-naphthalin-1-sulfonsaeure;

chromatotropic acid (148-25-4) → 4,5,4',5'-tetrahydroxy-3,3'-(3,3'-dihydroxy-biphenyl-4,4'-diyl-bis-azo)-bis-naphthalene-2,7-disulfonic acid

Conditions	Yield
With calcium hydroxide beim nachfolgenden Behandeln mit diazotiertem 3,3'-Dimethoxy-benzidin, CuSO4 und wss. NH3;

2-thiazolylamine (96-50-4) + chromatotropic acid (148-25-4) → 4,5-dihydroxy-3-thiazol-2-ylazo-naphthalene-2,7-disulfonic acid (28467-51-8)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) /BRN= 1827764/; Multistep reaction;

chromatotropic acid (148-25-4) + diazotized 4-amino-5-hydroxy-naphthalene-2,7-disulfonic acid → 4,5,5'-trihydroxy-3,4'-azo-bis-naphthalene-2,7-disulfonic acid (480-29-5)

Conditions	Yield
With sodium acetate

chromatotropic acid (148-25-4) + alkali → 1.3.8-trioxy-naphthalene-sulfonic acid-(6)

chromatotropic acid (148-25-4) + diazotized <2-amino-phenyl>-arsonic acid → arsenazo III (1668-00-4)

Upstream product

• 3316-02-7 1-naphthol-3,6,8-trisulphonic acid 
• 90-20-0 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid 
• 6362-11-4 1,8-diamino-3,6-naphthalenedisulfonic acid 
• 91-20-3 naphthalene 
• 188641-21-6 3-[(2,6-dibromo-4-methylphenyl)azo]-6[(2-sulfophenyl)azo]-4,5-dihydoxynaphthalene-2,7-disulfonic acid 
• 90-21-1 4-chloro-5-hydroxy-naphthalene-2,7-disulfonic acid 

Downstream Products

• 13432-13-8 3-benzeneazo-4,5-dihydroxynaphthalene-2,7-disulfonic acid 
• 121514-37-2 C₁₆H₁₃N₃O₁₁S₃ 
• 697756-74-4 C₂₆H₂₅N₅O₁₅S₃ 
• 31232-21-0 3-amino-4,5-dihydroxy-naphthalene-2,7-disulfonic acid 
• 24430-55-5 C₂₄H₁₆N₄O₁₂S₂ 
• 1681-60-3 3-(4-amino-phenylazo)-4,5-dihydroxy-naphthalene-2,7-disulfonic acid ; sodium salt 
• 62106-17-6 pontacyl violet 6R 
• 83656-13-7 2,7-Bis-(p-sulfophenylazo)-chromotropsaeure 
• 1668-00-4 arsenazo III 
• 28467-51-8 4,5-dihydroxy-3-thiazol-2-ylazo-naphthalene-2,7-disulfonic acid 
• 6837-94-1 4-ethoxy-5-hydroxy-naphthalene-2,7-disulfonic acid 

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