117-59-9

Basic information

• Product Name: 1-Naphthol-5-sulfonic acid
• Synonyms: 1-NAPHTHOL-5-SULFONIC ACID SODIUM SALT TECH;1,5-Oxy acid;1-Naphthalenesulfonic acid,5-hydroxy-;5-HYDROXY-1-NAPHTHALENESULFONIC ACID SODIUM SALT TECH;5-Hydroxy-1-naphthalenesulfonic acid;5-Hydroxynaphthalene-1-sulphonic acid;1-NAPHTHOL-5-SULFONICACID(L-ACID,DRY);5-Hydroxynaphthalene-1-sulfonic acid, 95+%
• CAS NO: 117-59-9
• Molecular Formula: C₁₀H₈O₄S
• Molecular Weight: 224.23
• EINECS: 204-199-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 117-59-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 110~112℃
• Appearance: off-white to reddish paste
• Density: 1.549 g/cm³
• Refractive Index: 1.703
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.26±0.40(Predicted)
• CAS DataBase Reference: 1-Naphthol-5-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthol-5-sulfonic acid(117-59-9)
• EPA Substance Registry System: 1-Naphthol-5-sulfonic acid(117-59-9)

Safety Data

• Hazardous Substances Data: 117-59-9(Hazardous Substances Data)

Usage

General Description

1-Naphthol-5-sulfonic acid is a chemical compound with the molecular formula C10H8O4S. It is a derivative of naphthalene and is a white to off-white crystalline powder. 1-Naphthol-5-sulfonic acid is used as a reagent in the synthesis of various organic compounds, especially dyes and pigments. It is also used as a pH indicator and in analytical chemistry to determine the presence of certain metals. Additionally, 1-Naphthol-5-sulfonic acid is employed in the production of pharmaceuticals and as an intermediate in the manufacture of agrochemicals. It is important to handle this chemical with care as it can cause skin and eye irritation if contact occurs.

InChI:InChI=1/C10H8O4S/c11-9-5-1-4-8-7(9)3-2-6-10(8)15(12,13)14/h1-6,11H,(H,12,13,14)

Synthetic route

1-aminonaphthalene-5-sulfonic acid (84-89-9) + furan-2,3,5(4H)-trione pyridine (1:1) → 5-amino-1-naphthol (83-55-6) + 1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + 1,5-dihydroxynaphthalene (83-56-7) + 1-amino-naphthalene (134-32-7)

Conditions	Yield
at 220 - 300℃; im Autoklaven;

1-aminonaphthalene-5-sulfonic acid (84-89-9) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With water; sodium hydrogensulfite at 100℃;

5-chloronaphthalene-1-sulfonic acid (89108-43-0) + furan-2,3,5(4H)-trione pyridine (1:1) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
at 240 - 250℃; unter Druck;

naphthalene-1,5-disulfonate (81-04-9) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With sodium hydroxide at 160 - 190℃; durch Verschmelzen;

5-oxo-5,6,7,8-tetrahydro-naphthalene-1,7-disulfonic acid (417712-00-6) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With hydroxide

naphthalene-1,5-disulfonate (81-04-9) + alkalies → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
at 160 - 190℃;

diazotized naphthylamine-(1)-sulfonic acid-(5) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With sulfuric acid

disodium- → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With sodium hydroxide; water at 260℃;

sodium salt of/the/ 1-chloro-naphthalene-sulfonic acid-(5) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

Conditions	Yield
With sodium hydroxide at 240 - 250℃;

sulfuric acid (7664-93-9) + 5-sulfo-naphthalene-1-diazonium-betaine (171290-14-5) → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9)

sodium 5-aminonaphthalene-1-sulfonate → 1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + diazo compound of m-nitro-aniline

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaHSO3 2: OH- View Scheme

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + 4-amino-o-xylene (95-64-7) → C18H16N2O4S

Conditions	Yield
Stage #1: 4-amino-o-xylene With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.5h; Stage #2: 1-hydroxynaphthalene-5-sulphonic acid With sodium hydroxide In water at 10℃; pH=8.8 - 9.3;	99.5%

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + 4-nitro-aniline (100-01-6) → 5-Hydroxy-6-(4-nitro-phenylazo)-naphthalene-1-sulfonic acid

Conditions	Yield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 80℃; for 1.33333h; Stage #2: 1-hydroxynaphthalene-5-sulphonic acid With sodium hydroxide In water at 10℃; pH=8.8 - 9.3;	99.2%

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + dimethyl sulfate (77-78-1) → 5-Methoxynaphtalin-1-sulfonsaeure (86124-67-6)

Conditions	Yield
With sodium hydroxide In water	95%

ammonium bisulfite + α-naphthol (90-15-3) + 1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + 1,5-dihydroxynaphthalene (83-56-7) → 1,5-diaminonaphthalene (2243-62-1)

Conditions	Yield
With sodium hydroxide; sulfur dioxide; ammonia In titanium; water	86%

benzenediazonium (2684-02-8) + 1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 5-hydroxy-6-phenylazo-naphthalene-1-sulfonic acid

Conditions	Yield
beim Behandeln von Benzoldiazoniumsalz;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + benzene diazonium chloride (100-34-5) → 5-hydroxy-6-phenylazo-naphthalene-1-sulfonic acid

Conditions	Yield
in natronalkalischer Loesung;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 1,5-dihydroxynaphthalene (83-56-7)

Conditions	Yield
With potassium carbonate beim Schmelzen;
With potassium carbonate at 200℃;
With sodium hydroxide at 220 - 260℃; beim Schmelzen;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 6-hydroxyimino-5-oxo-5,6-dihydro-naphthalene-1-sulfonic acid

Conditions	Yield
With hydrogenchloride; sodium nitrite

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 8-amino-5-hydroxy-naphthalene-1-sulfonic acid

Conditions	Yield
With 2,5-dichlorobenzenediazonium Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;
With 2,4,5-Trichlor-benzoldiazonium Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;
With 3-nitro-4-chlorobenzenediazonium cation Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;
With C6H4N3O5S(1+) Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 2-amino-1-naphthol-5-sulfonic acid (573-07-9)

Conditions	Yield
With 4-chlorophenyldiazonium salt Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;
With 4-diazobenzenesulfonic acid Reduktion der entstehenden Azofarbstoffe mit Zinnchloruer und Salzsaeure;
Multi-step reaction with 2 steps 1: in natronalkalischer Loesung 2: tin dichloride; hydrochloric acid View Scheme

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 1,5-dihydroxy-naphthalene-2-sulfonic acid (149141-81-1)

Conditions	Yield
durch folgeweise Sulfurierung und Kalischmelze;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 5-hydroxy-naphthalene-1,6-disulfonic acid

Conditions	Yield
With sulfuric acid

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + chloroformic acid ethyl ester (541-41-3) → 5-ethoxycarbonyloxy-naphthalene-1-sulfonic acid

Conditions	Yield
With alkali

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + Benzotrichlorid (98-07-7) → 6-benzoyl-5-hydroxy-naphthalene-1-sulfonic acid

Conditions	Yield
With sulfuric acid at 20℃;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) + benzoyl chloride (98-88-4) → 2-phenyl-naphtho[2,1-d]oxazole-6-sulfonic acid (2032-01-1)

Conditions	Yield
(i) 3-diazoniumbenzene sulfonate, aq. Na2CO3, (ii) aq. Na2S2O4, (iii) /BRN= 471389/, (iv) H2SO4; Multistep reaction;

1-hydroxynaphthalene-5-sulphonic acid (117-59-9) → 2,6-Dihydroxybenzoic acid (303-07-1)

Conditions	Yield
at 27℃; for 24h; Product distribution; Pseudomonas sp. TA-2 cells, phosphate buffer; metabolism, degradation pathway;

Upstream product

• 81-04-9 naphthalene-1,5-disulfonate 
• 7664-93-9 sulfuric acid 
• 171290-14-5 5-sulfo-naphthalene-1-diazonium-betaine 
• 417712-00-6 5-oxo-5,6,7,8-tetrahydro-naphthalene-1,7-disulfonic acid 
• 89108-43-0 5-chloronaphthalene-1-sulfonic acid 
• 84-89-9 1-aminonaphthalene-5-sulfonic acid 

Downstream Products

• 83-56-7 1,5-dihydroxynaphthalene 
• 573-07-9 2-amino-1-naphthol-5-sulfonic acid 
• 606-41-7 2-amino-1-naphthol 
• 2243-62-1 1,5-naphthalenediamine 
• 90-15-3 α-naphthol 
• 83-55-6 5-amino-1-naphthol 
• 303-07-1 2,6-Dihydroxybenzoic acid 
• 2032-01-1 2-phenyl-naphtho[2,1-d]oxazole-6-sulfonic acid 

Relevant articles and documents

Process for aryl-quinone and aryl-naphthoquinone diazide sulfonic acids

A process for the preparation of aryl-diazide-sulfonic acids by a series of sequential in-situ process steps. The process comprises the nitrosation of a hydroxyarylsulfonic acid; conversion of the nitroso-derivative to a sulfamate which is then diazotized to the diazide. Temperature and pH are maintained in predetermined ranges to maintain the reaction products in solution without the formation side-products or the need to isolate intermediates. The process of the invention is particularly useful in the preparation of light-sensitive materials such as naphthoquinonediazide sulfonic acids which are used in the preparation of photoresist compositions. The invention provides a high purity product at a high material efficiency, high equipment utilization, low effluent discharge, and reduced cost.