88-23-3

Basic information

• Product Name: 2-Amino-4-chlorophenol-6-sulfonic acid
• Synonyms: Metanilic acid, 5-chloro-2-hydroxy-;Metanilic acid, 5-chloro-2-hydroxy- (8CI);3-amino-5-chloro-2-hydroxy-benzenesulfonicaci;2-AMINO-4-CHLOROPHENOL-6-SULFONIC ACID;3-AMINO-5-CHLORO-2-HYDROXYBENZENESULFONIC ACID;4-CHLORO-2-AMINOPHENOL-6-SULFONIC ACID;6-amino-4-chloro-1-phenol-2-sulfonic acid;3-amino-5-chloro-2-hydroxybenzenesulphonic acid
• CAS NO: 88-23-3
• Molecular Formula: C₆H₆ClNO₄S
• Molecular Weight: 223.63
• EINECS: 201-813-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 88-23-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 150°C4mm Hg(lit.)
• Flash Point: >230°F
• Appearance: Off-white solid
• Density: 1.79 g/cm³
• Refractive Index: 1.677
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -1.53±0.50(Predicted)
• CAS DataBase Reference: 2-Amino-4-chlorophenol-6-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chlorophenol-6-sulfonic acid(88-23-3)
• EPA Substance Registry System: 2-Amino-4-chlorophenol-6-sulfonic acid(88-23-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-24/25-26-39
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 88-23-3(Hazardous Substances Data)

Usage

Air & Water Reactions

May be sensitive to prolonged exposure to air and/or light. Insoluble in water.

Reactivity Profile

2-Amino-4-chlorophenol-6-sulfonic acid may react with strong oxidizing or reducing agents and with mineral acids and bases

Fire Hazard

Flash point data are not available for 2-Amino-4-chlorophenol-6-sulfonic acid, but 2-Amino-4-chlorophenol-6-sulfonic acid is probably combustible.

InChI:InChI=1/C6H6ClNO4S/c7-3-1-4(8)6(9)5(2-3)13(10,11)12/h1-2,9H,8H2,(H,10,11,12)

Synthetic route

5-chloro-2-hydroxy-3-nitro-benzenesulfonic acid (88-25-5) → 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3)

2-hydroxy-5-chloro-aniline (95-85-2) → 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3)

Conditions	Yield
With sulfuric acid
With sulfuric acid

N-(5-chloro-2-hydroxyphenyl)acetamide (26488-93-7) → 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3)

Conditions	Yield
durch Sulfurieren und Verseifen des Reaktionsproduktes;
durch Sulfurien und Verseifen des Reaktionsproduktes;

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + acetylacetone (123-54-6) → 3-(5-chloro-2-hydroxy-3-sulfophenylhydrazo)pentane-2,4-dione (1246887-50-2)

Conditions	Yield
Stage #1: 2-amino-4-chlorophenol-6-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; Stage #2: acetylacetone With sodium hydroxide In water Cooling with ice;	77%

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + 1-phenylbutan-1,3-dione (93-91-4) → 1-phenyl-2-(2-hydroxy-3-sulfo-5-chlorophenylhydrazo)butane-1,3-dione

Conditions	Yield
Stage #1: 2-amino-4-chlorophenol-6-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; Japp-Klingemann reaction; Stage #2: 1-phenylbutan-1,3-dione With sodium acetate In ethanol; water Japp-Klingemann reaction; Cooling with ice;	77%

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + dimedone (126-81-8) → 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-benzenesulfonic acid (1393845-94-7)

Conditions	Yield
Stage #1: 2-amino-4-chlorophenol-6-sulfonic acid With sodium hydroxide; sodium nitrite In water at -0.16℃; Stage #2: With hydrogenchloride In water at 4.84℃; for 1h; Stage #3: dimedone With sodium hydroxide In ethanol; water at -0.16℃; Japp-Klingemann Hydrazone Synthesis;	75%

2-(3,4-dimethylphenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one (277299-70-4) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 5-chloro-3-{[1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]azo}-2-hydroxybenzenesulfonic acid

Conditions	Yield
	34%

phosgene (75-44-5) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 5-chloro-2-oxo-2,3-dihydro-benzoxazole-7-sulfonic acid

Conditions	Yield
With sodium hydroxide at 5 - 10℃;

2-methyl-5-nitrobenzene-1-sulfonyl chloride (121-02-8) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-(4-amino-toluene-2-sulfonylamino)-5-chloro-2-hydroxy-benzenesulfonic acid (6528-45-6)

Conditions	Yield
nachfolgend Reduktion;

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-amino-5-chloro-2-hydroxy-benzenesulfonyl chloride

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 5-chloro-3-hydrazino-2-hydroxy-benzenesulfonic acid

Conditions	Yield
Diazotization.Erhitzen der Diazoverbindung mit NaHSO3-Loesung und Soda und Kochen des Reaktionsprodukts mit verd. Schwefelsaeure;

bromocyane (506-68-3) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 2-amino-5-chloro-benzooxazole-7-sulfonic acid (64037-29-2)

Conditions	Yield
(i) MeOH, (ii) H2O; Multistep reaction;

phosgene (75-44-5) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + furan-2,3,5(4H)-trione pyridine (1:1) → 5-chloro-benzoxazolone-sulfonic acid-(7)

Conditions	Yield
at 5 - 10℃;

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 5-chloro-2-hydroxy-3-(3-methyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-benzenesulfonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: Diazotization.Erhitzen der Diazoverbindung mit NaHSO3-Loesung und Soda und Kochen des Reaktionsprodukts mit verd. Schwefelsaeure View Scheme

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 1-(5-chloro-2-hydroxy-3-sulfo-phenyl)-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: Diazotization.Erhitzen der Diazoverbindung mit NaHSO3-Loesung und Soda und Kochen des Reaktionsprodukts mit verd. Schwefelsaeure 2: natrium carbonate View Scheme

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → (2S)-2-amino-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]butanoic acid (1220125-05-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diisopropyl-carbodiimide; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C 2: trifluoroacetic acid / 20 °C View Scheme
Stage #1: 2-amino-4-chlorophenol-6-sulfonic acid; N-tert-butoxycarbonyl glutamic acid tert-butyl ester With pyridine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Stage #2: With trifluoroacetic acid at 20℃; for 1.5h;
Multi-step reaction with 2 steps 1: triethylamine; benzotriazol-1-ol; diisopropyl-carbodiimide / N,N-dimethyl-formamide / 0 - 20 °C 2: trifluoroacetic acid / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; diisopropyl-carbodiimide; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: trifluoroacetic acid / 2 h / 20 °C View Scheme

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → C20H29ClN2O9S (1333219-82-1)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃;
With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃;

Cbz-(L)-Glu-OBn (3705-42-8) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → N5-(2-hydroxy-3-sulfophenyl)-L-glutamine (1220125-08-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 20 °C 1.2: 20 °C 2.1: hydrogen / palladium on carbon / water; methanol / 20 °C View Scheme

Cbz-(L)-Glu-OBn (3705-42-8) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → C26H25ClN2O9S

Conditions	Yield
Stage #1: Cbz-(L)-Glu-OBn With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 2-amino-4-chlorophenol-6-sulfonic acid In tetrahydrofuran; dichloromethane at 20℃;

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + ethyl acetoacetate (141-97-9) → C12H13ClN2O7S

Conditions	Yield
Stage #1: 2-amino-4-chlorophenol-6-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 4.84℃; for 1h; Cooling with ice; Stage #2: ethyl acetoacetate With sodium acetate In ethanol at -0.16℃; for 1h; Cooling with ice;

Boc-Glu(OBzl)-OH (13574-13-5) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + benzylamine (100-46-9) → 3-[(4S)-4-amino-4-(benzylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333218-58-8)

Conditions	Yield
Stage #1: Boc-Glu(OBzl)-OH; benzylamine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane Stage #2: With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 2h; Stage #3: 2-amino-4-chlorophenol-6-sulfonic acid

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid (45214-91-3) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + phenethylamine (64-04-0) → 3-[(4S)-4-amino-4-[(2-phenylethyl)carbamoyl]butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333218-59-9)

Conditions	Yield
Stage #1: (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid; phenethylamine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane Stage #2: With lithium hydroxide In tetrahydrofuran; methanol; water Stage #3: 2-amino-4-chlorophenol-6-sulfonic acid	151.9 mg

methanesulfonamide (3144-09-0) + Boc-Glu(OBzl)-OH (13574-13-5) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-[(45)-4-amino-4-(methanesulfonylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333218-70-4)

Conditions

Yield

Stage #1: methanesulfonamide; Boc-Glu(OBzl)-OH With dmap; triethylamine In dichloromethane at 20℃; Stage #2: With palladium 10% on activated carbon; hydrogen In ethyl acetate Stage #3: 2-amino-4-chlorophenol-6-sulfonic acid With 1-hydroxy-7-aza-benzotriazole; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide

15.3 mg

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) + N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → (2S)-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]-2-(dimethylamino)butanoic acid (1333219-13-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-hydroxy-7-aza-benzotriazole; pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 1.2: 1.5 h / 20 °C 2.1: hydrogen; palladium 10% on activated carbon / water View Scheme

(4S)-4-(N-tert-butoxycarbonylamino)-4-(5-ethyl-1,3,4-oxadiazole-2-yl)butanoic acid (1333219-62-7) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-[(4S)-4-(N-tert-butoxycarbonylamino)-4-(5-ethyl-1,3,4-oxadiazole-2-yl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333219-63-8)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;	9 mg

(4S)-4-(N-tert-butoxycarbonylamino)-4-(ethylcarbamoyl)butanoic acid (70962-77-5) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-[(4S)-4-(N-tert-butoxycarbonylamino)-4-(ethylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333219-64-9)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane

tert-butyl (2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride (1333246-31-3) + 2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → (2S)-2-amino-3-{[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]amino}propanoic acid (1333218-42-0)

Conditions	Yield
Stage #1: tert-butyl (2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride; 2-amino-4-chlorophenol-6-sulfonic acid With pyridine; bis(trichloromethyl) carbonate In dichloromethane at 20℃; Stage #2: With trifluoroacetic acid In dichloromethane for 5h;	20.1 mg

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → (2S)-2-amino-3-{[(2-hydroxy-3-sulfophenyl)carbamoyl] amino} propanoic acid (1333218-64-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bis(trichloromethyl) carbonate; pyridine / dichloromethane / 20 °C 1.2: 5 h 2.1: hydrogen; palladium on activated charcoal / water; methanol / 72 h View Scheme

2-amino-4-chlorophenol-6-sulfonic acid (88-23-3) → 3-[(4S)-4-(N-tert-butoxycarbonylamino)-4-(5-ethyl-1,3,4-oxadiazole-2-yl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid (1333219-63-8)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;

Upstream product

• 26488-93-7 N-(5-chloro-2-hydroxyphenyl)acetamide 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 88-25-5 5-chloro-2-hydroxy-3-nitro-benzenesulfonic acid 

Downstream Products

• 1336933-83-5 C₁₆H₂₁ClN₂O₉S 
• 1336933-77-7 C₁₈H₂₅ClN₂O₉S 
• 1333218-45-3 3-({[(2S)-2-amino-3-phenylpropoxy]carbonyl}amino)-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333218-43-1 3-({[(2S)-2-amino-propoxy]carbonyl}amino)-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333218-89-5 3-[(4S)-4-amino-4-(5-ethyl-1,3,4-oxadiazole-2-yl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333219-63-8 3-[(4S)-4-(N-tert-butoxycarbonylamino)-4-(5-ethyl-1,3,4-oxadiazole-2-yl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333218-64-6 (2S)-2-amino-3-{[(2-hydroxy-3-sulfophenyl)carbamoyl] amino} propanoic acid 
• 1333218-42-0 (2S)-2-amino-3-{[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]amino}propanoic acid 
• 1333219-64-9 3-[(4S)-4-(N-tert-butoxycarbonylamino)-4-(ethylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333219-13-8 (2S)-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]-2-(dimethylamino)butanoic acid 
• 1333218-70-4 3-[⁽⁴⁵⁾-4-amino-4-(methanesulfonylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333218-59-9 3-[(4S)-4-amino-4-[(2-phenylethyl)carbamoyl]butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1333218-58-8 3-[(4S)-4-amino-4-(benzylcarbamoyl)butanamide]-5-chloro-2-hydroxybenzene-1-sulfonic acid 
• 1393845-94-7 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-benzenesulfonic acid 

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