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

Description

CI 13015, also known as Sodium (E)-4-(2,4-Dihydroxyphenyl)diazenyl)benzenesulfonate, is an organic compound that is used as an azo dye. It is characterized by its yellow-orange color and is soluble in water, ethanol, and acetone, but insoluble in other organic solvents. The color of its solutions can vary depending on the acidity or alkalinity of the solution, with strong sulfuric acid turning it yellow and diluted solutions turning it lemon yellow. It is also known for its light fastness, soaping fastness, perspiration fastness, oxygen bleaching, and fastness to seawater.

Uses

Used in Dye Industry:
CI 13015 is used as a dye for various types of fibers, including wool, silk, cotton, and polyamide fibers. It is also used for dyeing leather and biological materials.
Used in Environmental Testing:
CI 13015 is used as an indicator in environmental testing, with a pH range of 12 to 14.
Used in Food Industry:
CI 13015 is used as a dye in the food industry, specifically as an azo dye.
Chemical Properties:
CI 13015 is a rust to dark brown powder that is soluble in water, ethanol, and acetone, but insoluble in other organic solvents. Its color can vary depending on the acidity or alkalinity of the solution, with strong sulfuric acid turning it yellow and diluted solutions turning it lemon yellow. It is also known for its light fastness, soaping fastness, perspiration fastness, oxygen bleaching, and fastness to seawater.

Preparation

4-Aminobenzenesulfonic acid diazo, Coupled with resorcinol.

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.