547-57-9

Basic information

• Product Name: CI 13015
• Synonyms: 4-((2,4-dihydroxyphenyl)azo)-benzenesulfonicacimonosodiumsalt;4-[(2,4-dihydroxyphenyl)azo]-benzenesulfonicacimonosodiumsalt;acidleatheryellowpgw;acidphosphinegnew;acmeyellowacidyellowrs;Benzenesulfonicacid,4-[(2,4-dihydroxyphenyl)azo]-,monosodiumsalt;c.i.acidorange6;c.i.acidorange6,monosodiumsalt
• CAS NO: 547-57-9
• Molecular Formula: C₁₂H₉N₂O₅S*Na
• Molecular Weight: 316.27
• EINECS: 208-924-8
• Product Categories: Organics;Analytical Chemistry;Indicator (pH);pH Indicators;Azo
• Mol File: 547-57-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: >300°C
• Appearance: Rust to dark brown/Powder
• Storage Temp.: Room Temperature
• Solubility: Solubility Soluble in water, ethanol
• PKA: 11.5, 11.9(at 25℃)
• Water Solubility: Soluble in water and alcohol
• Merck: 14,9775
• BRN: 4173410
• CAS DataBase Reference: CI 13015(CAS DataBase Reference)
• NIST Chemistry Reference: CI 13015(547-57-9)
• EPA Substance Registry System: CI 13015(547-57-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 1
• RTECS: DB5035000
• TSCA: Yes
• Hazardous Substances Data: 547-57-9(Hazardous Substances Data)

Usage

Chemical Properties

Rust to dark brown powder

Uses

Different sources of media describe the Uses of 547-57-9 differently. You can refer to the following data:
1. As indicator. pH: yellow 11, orange-brown 12.7. Occasionally used as plasma stain.
2. Sodium (E)-4-(2, 4-Dihydroxyphenyl)diazenyl)benzenesulfonate is a food and an azo dye. Dyes and metabolites, Environmental Testing

Preparation

4-Aminobenzenesulfonic acid diazo, Coupled with resorcinol.

Properties and Applications

yellow orange. Soluble in water for golden brown, soluble in ethanol lemon yellow, soluble in acetone and soluble fiber element, insoluble in other organic solvents. The strong sulfuric acid for yellow, diluted for lemon yellow; In nitric acid solution for yellow. Its water solution to join strong hydrochloric acid for golden brown; Add thick sodium hydroxide solution for palm orange. Used for wool, silk, cotton, vinegar, polyamide fiber and fiber dyeing. Also used in leather, biological dyeing, also used in indicator (pH 12 ~ 14). Standard Light Fastness Soaping Persperation Fastness Oxygen bleaching Fastness to seawater Fading Stain Fading Stain Fading Stain ISO 4-5 3 2 1-2 3 AATCC 3-4 4 1 1 3

Standard

Light Fastness

Fading

Stain

ISO

4-5

AATCC

3-4

InChI:InChI=1/C12H10N2O5S.Na/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19;/h1-7,15-16H,(H,17,18,19);/q;+1/p-1/b14-13+;

Synthetic route

recorcinol (108-46-3) + 4-aminobenzene sulfonic acid (121-57-3) → tropaeolin O (547-57-9)

Conditions	Yield
With sodium nitrite at 0℃; Neat (no solvent);	70%

Sulfathiazole (72-14-0) + tropaeolin O (547-57-9) → C21H15N6O7S3(1-)*Na(1+) (1312665-63-6)

Conditions	Yield
Stage #1: Sulfathiazole With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

sulfamethoxazole (723-46-6) + tropaeolin O (547-57-9) → C22H17N6O8S2(1-)*Na(1+) (1312665-61-4)

Conditions	Yield
Stage #1: sulfamethoxazole With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

sulfadiazine (68-35-9) + tropaeolin O (547-57-9) → C22H16N7O7S2(1-)*Na(1+) (1312665-62-5)

Conditions	Yield
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

sulfamerazina (127-79-7) + tropaeolin O (547-57-9) → C23H18N7O7S2(1-)*Na(1+) (1312665-58-9)

Conditions	Yield
Stage #1: sulfamerazina With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

sulfadimesine (57-68-1) + tropaeolin O (547-57-9) → C24H20N7O7S2(1-)*Na(1+) (1312665-59-0)

Conditions	Yield
Stage #1: sulfadimesine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

Sulfamethoxypyridazine (80-35-3) + tropaeolin O (547-57-9) → C23H18N7O8S2(1-)*Na(1+) (1312665-66-9)

Conditions	Yield
Stage #1: Sulfamethoxypyridazine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

sulphadimethoxine (155-91-9) + tropaeolin O (547-57-9) → C24H20N7O9S2(1-)*Na(1+) (1312665-60-3)

Conditions	Yield
Stage #1: sulphadimethoxine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

tropaeolin O (547-57-9) + sulfanilamide (63-74-1) → C18H14N5O7S2(1-)*Na(1+) (1312665-57-8)

Conditions	Yield
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

tropaeolin O (547-57-9) + sulfamonomethoxine (1220-83-3) → C23H18N7O8S2(1-)*Na(1+) (1312665-65-8)

Conditions	Yield
Stage #1: sulfamonomethoxine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

tropaeolin O (547-57-9) + 1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene (57-67-0) → C19H16N7O7S2(1-)*Na(1+) (1312665-64-7)

Conditions	Yield
Stage #1: 1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

Upstream product

• 108-46-3 recorcinol 
• 121-57-3 4-aminobenzene sulfonic acid 

Downstream Products

• 1312665-63-6 C₂₁H₁₅N₆O₇S₃^(1-)*Na⁽¹⁺⁾ 
• 1312665-61-4 C₂₂H₁₇N₆O₈S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-62-5 C₂₂H₁₆N₇O₇S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-58-9 C₂₃H₁₈N₇O₇S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-59-0 C₂₄H₂₀N₇O₇S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-66-9 C₂₃H₁₈N₇O₈S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-60-3 C₂₄H₂₀N₇O₉S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-57-8 C₁₈H₁₄N₅O₇S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-65-8 C₂₃H₁₈N₇O₈S₂^(1-)*Na⁽¹⁺⁾ 
• 1312665-64-7 C₁₉H₁₆N₇O₇S₂^(1-)*Na⁽¹⁺⁾ 

Relevant articles and documents

Can be azo dyes obtained by grinding under solvent-free conditions?

The solid-solid reactions of some electron-donors with sulfanilic acid in the presence of solid sodium nitrite afford azo dyes by self-catalyzed diazotization of sulfanilic acid (2) under solvent-free conditions with moderate yields. Also the reactions of some electron-donors with diazotization of o-nitroaniline (5), m-nitroaniline (6) and p-nitroaniline (7) in the presence of solid sodium nitrite catalyzed by p-toluenesulfonic acid (PTSA) afford azo dyes under solvent-free conditions in good yields. This new method totally avoids the use of acids, alkalies, and toxic and/or expensive solvents in diazotization and diazo coupling reactions.