119-28-8

Basic information

• Product Name: 1-Naphthylamine-7-sulfonic acid
• Synonyms: TIMTEC-BB SBB000621;SODIUM NAPTHIONATE;SODIUM NAPHTHIONATE;SODIUM 1-NAPHTHYLAMINE-4-SULFONATE;PARA-NAPHTHIONIC ACID, NA SALT;NAPHTHIONIC ACID SODIUM SALT 0.5-WATER;NAPHTHIONIC ACID SODIUM SALT;NAPHTHYLAMINE-4-SULFONIC ACID SODIUM SALT
• CAS NO: 119-28-8
• Molecular Formula: C₁₀H₉NO₃S
• Molecular Weight: 223.25
• EINECS: 204-311-4
• Product Categories: Intermediates of Dyes and Pigments;Intermediates
• Mol File: 119-28-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Boiling Point: 220°C (rough estimate)
• Appearance: /
• Density: 1.3588 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pK1: 3.66 (25°C)
• Merck: 14,2351
• BRN: 2115629
• CAS DataBase Reference: 1-Naphthylamine-7-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthylamine-7-sulfonic acid(119-28-8)
• EPA Substance Registry System: 1-Naphthylamine-7-sulfonic acid(119-28-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 119-28-8(Hazardous Substances Data)

Usage

Synthesis

1-Naphthylamine-7-sulfonic acid can be obtained by sulfonation, nitration, neutralization, reduction and acid precipitation of naphthalene.

Chemical Properties

Brown crystalline

Uses

Different sources of media describe the Uses of 119-28-8 differently. You can refer to the following data:
1. Intermediate of dyestuff
2. 8-Amino-2-naphthalenesulfonic acid can be used as a reactant to synthesize: Fe3O4/sulfonated polyaniline composite material via chemical oxidative polymerization with aniline in the presence of magnetite (Fe3O4) nanoparticles. Prismatic crystals of strychnine-8-ammonio-2-naphthalenesulfonate-water by heating with strychnine in water/ethanol solvent mixture.5-amino-9-dialkylamino benzo[a]phenoxazine dyes (Nile blue analogs) by condensation with N-alkyl or N-sulfo-propyl 4-arylazo-substituted 3-hydroxyaniline.

Application

1-Naphthylamine-7-sulfonic acid can be used as a dye intermediate to prepare dyes such as direct light fast blue B2RL, direct light fast red brown RTL, and sulfur blue CV.

InChI:InChI=1/C10H9NO3S/c11-10-3-1-2-7-4-5-8(6-9(7)10)15(12,13)14/h1-6H,11H2,(H,12,13,14)

Synthetic route

naphthalene-2-sulfonate (120-18-3) → 5-aminonaphthalene-2-sulfonic acid (119-79-9) + 8-amino-2-naphthalenesulfonic acid (119-28-8)

Conditions	Yield
With sulfuric acid; nitric acid at 25℃; anschl. bei 10grad, Reduzieren des erhaltenen Gemisches mit Eisen und sehr verd. Salzsaeure;
With sulfuric acid; nitric acid at 25℃; dann bei 10grad, Reduzieren des erhaltenen Gemisches mit Eisen und sehr verd. Salzsaeure;
Stage #1: naphthalene-2-sulfonate With sulfuric acid at 120℃; for 0.666667h; Stage #2: With nitric acid at 33 - 35℃; for 20h; Reagent/catalyst; Overall yield = 86 percent; Overall yield = 75 g; Further stages;

1-nitro-7-naphthalenesulfonic acid (18425-74-6) → 8-amino-2-naphthalenesulfonic acid (119-28-8)

Conditions	Yield
With ammonium sulfide
With iron; acetic acid

8-hydroxy-naphthalene-2-sulfonic acid (20191-62-2) + sodium disulfite → 8-amino-2-naphthalenesulfonic acid (119-28-8)

Conditions	Yield
Reaktion des Natriumsalzes; Erhitzen des Reaktionsprodukts mit Ammoniak unter Druck auf 100-110grad, dann beim Ansaeuern;

sulfuric acid (7664-93-9) + 1-amino-naphthalene-2,7-disulfonic acid (486-54-4) → 8-amino-2-naphthalenesulfonic acid (119-28-8)

1-amino-naphthalene-2,7-disulfonic acid (486-54-4) + water (7732-18-5) → 8-amino-2-naphthalenesulfonic acid (119-28-8)

Conditions	Yield
unter Druck;

1-nitro-7-naphthalenesulfonic acid (18425-74-6) + ammonium sulfide → 8-amino-2-naphthalenesulfonic acid (119-28-8)

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-hydroxy-naphthalene-2-sulfonic acid (20191-62-2)

Conditions	Yield
Stage #1: 8-amino-2-naphthalenesulfonic acid With water; sodium hydrogensulfite for 15h; Reflux; Inert atmosphere; Stage #2: With sodium hydroxide In water for 4h; Reflux; Stage #3: With hydrogenchloride In water	95%
With sodium disulfite man kocht und macht alkalisch;
With sodium hydroxide at 260℃;

8-amino-2-naphthalenesulfonic acid (119-28-8) + 3,4-dichlorobenzoyl chloride (3024-72-4) → 8-(3,4-dichlorobenzamido)naphthalene-2-sulfonic acid (1415094-32-4)

Conditions	Yield
With pyridine at 20℃; for 12h; Inert atmosphere;	91%

8-amino-2-naphthalenesulfonic acid (119-28-8) + 4-nitro-aniline (100-01-6) → 8-amino-5-(4-nitro-phenylazo)-2-naphthalenesulfonic acid

Conditions	Yield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.333333h; Stage #2: 8-amino-2-naphthalenesulfonic acid In methanol; water at 20℃; for 0.5h;	90%

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-5,8'-azo-bis-naphthalene-2-sulphonic acid

Conditions	Yield
With hydrogenchloride; sodium nitrite at 55℃; for 0.5h; pH=2;	87%
With ethanol; nitrate radical

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-chloro-naphthalene-2-sulfonic acid (42849-62-7)

Conditions	Yield
Stage #1: 8-amino-2-naphthalenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride; copper(l) chloride In water at 0 - 20℃; for 13h; Inert atmosphere;	65%
durch Austausch von NH2 gegen Chlor;

8-amino-2-naphthalenesulfonic acid (119-28-8) + phenylhydrazine (100-63-0) → sodium 1-phenylazonaphthalene-7-sulfonate

Conditions	Yield
With sodium hydrogencarbonate at 140 - 150℃; for 24h;	43%

8-amino-2-naphthalenesulfonic acid (119-28-8) → poly(5-aminonaphthalene-2-sulphonic acid)

Conditions	Yield
With sodium hydroxide; sodium persulfate In water at 20℃; for 16h; oxidative polymerization;	31%

8-amino-2-naphthalenesulfonic acid (119-28-8) + benzene-1,3-dicarbonyl dichloride (99-63-8) → disodium 8,8'-[1,3-phenylenebis(carbonylimino)]bis(2-naphthalenesulfonate)

Conditions	Yield
With sodium carbonate In chloroform; water at 25℃; for 18h;	28%

benzenediazonium (2684-02-8) + 8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-5-phenylazo-naphthalene-2-sulfonic acid (68121-31-3)

8-amino-2-naphthalenesulfonic acid (119-28-8) + benzene diazonium chloride (100-34-5) → 5,8-diamino-naphthalene-2-sulfonic acid (6357-90-0)

Conditions	Yield
With sodium acetate Reduzieren mit Zinn(II)-chlorid und Salzsaeure;

8-amino-2-naphthalenesulfonic acid (119-28-8) + 3-carboxylato-4-hydroxybenzenediazonium (68596-89-4) → 2-hydroxy-5-[4-(2-hydroxy-3-phenylcarbamoyl-[1]naphthylazo)-6-sulfo-[1]naphthylazo]-benzoic acid

Conditions	Yield
diazotiert wieder und kuppelt mit 3-Oxy-naphthoesaeure-(2)-anilid in sodaalkalischer Loesung;

8-amino-2-naphthalenesulfonic acid (119-28-8) + furan-2,3,5(4H)-trione pyridine (1:1) → 1,7-Dihydroxynaphthalene (575-38-2) + 8-amino-2-naphthol (118-46-7) + 8-hydroxy-naphthalene-2-sulfonic acid (20191-62-2)

Conditions	Yield
at 260℃; unter Druck;

8-amino-2-naphthalenesulfonic acid (119-28-8) → benzo[h]quinolin-9-ol (57442-06-5)

Conditions	Yield
ueber Benzo<h>chinolin-9-sulfonsaeure;

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-2-naphthol (118-46-7)

Conditions	Yield
With sodium hydroxide; water at 250 - 260℃;
With sodium hydroxide; water
With sodium hydroxide at 280 - 320℃; for 10h; Autoclave;

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid (483-84-1)

Conditions	Yield
With hydrogenchloride; sodium nitrite Diazotization.und Behandeln des Reaktionsprodukts mit Salpetersaeure;

8-amino-2-naphthalenesulfonic acid (119-28-8) → 1-aminonaphthalene-2,4,7-trisulphonic acid (61986-93-4)

Conditions	Yield
With sulfuric acid

8-amino-2-naphthalenesulfonic acid (119-28-8) → 7-sulfo-[1]naphthoic acid (861511-44-6)

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-5,7-dibromo-naphthalene-2-sulfonic acid

Conditions	Yield
With hydrogenchloride; bromine

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-5-nitro-naphthalene-2-sulfonic acid (6357-78-4)

Conditions	Yield
With sulfuric acid; nitric acid

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-ethanesulfonyl-naphthalene-2-sulfonic acid amide (105905-81-5)

Conditions	Yield
ueber 8-Aethylmercapto-naphthalin-2-sulfonsaeure-amid;
Multi-step reaction with 4 steps 1.1: potassium hydroxide; sulfuric acid; potassium nitrite / water / 0.75 h / 0 - 20 °C / Inert atmosphere 1.2: 3.08 h / 20 °C / Heating; Inert atmosphere 2.1: trichlorophosphate / 2 h / Reflux; Inert atmosphere 2.2: 20 °C / Cooling with ice; Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 24 h / 50 - 125 °C / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere View Scheme

8-amino-2-naphthalenesulfonic acid (119-28-8) → 8-amino-5-nitroso-naphthalene-2-sulfonic acid

Conditions	Yield
With sulfuric acid; sodium nitrite

8-amino-2-naphthalenesulfonic acid (119-28-8) → 7-sulfo-naphthalene-1-diazonium-betaine

Conditions	Yield
With ethanol; nitrate radical
With sulfuric acid; sodium nitrite at 0℃; Kinetik der Bildung;

8-amino-2-naphthalenesulfonic acid (119-28-8) + acetic anhydride (108-24-7) → 8-acetylamino-naphthalene-2-sulfonic acid (118-37-6)

Conditions	Yield
With pyridine

8-amino-2-naphthalenesulfonic acid (119-28-8) + p-toluidine (106-49-0) → 8-p-toluidino-naphthalene-2-sulfonic acid (899-76-3)

Conditions	Yield
With p-toluidine hydrochloride at 160 - 170℃;

2-diazo-1-(4-nitrophenyl)ethanone (4203-31-0) + 8-amino-2-naphthalenesulfonic acid (119-28-8) + benzoyl chloride (98-88-4) → 8-benzoylamino-naphthalene-2-sulfonic acid-(4-nitro-phenacyl ester) (102884-85-5)

Conditions	Yield
With copper dichloride

8-amino-2-naphthalenesulfonic acid (119-28-8) + acetic acid (64-19-7) → 8-acetylamino-naphthalene-2-sulfonic acid (118-37-6)

Conditions	Yield
With sodium acetate

8-amino-2-naphthalenesulfonic acid (119-28-8) + aniline hydrochloride (142-04-1) + aniline (62-53-3) → 8-anilino-1-naphthalenesulfonic acid (607-13-6)

Conditions	Yield
at 160 - 170℃;

8-amino-2-naphthalenesulfonic acid (119-28-8) + aniline (62-53-3) → 8-anilino-1-naphthalenesulfonic acid (607-13-6)

Conditions	Yield
With aniline hydrochloride at 160 - 170℃;

Upstream product

• 120-18-3 naphthalene-2-sulfonate 
• 18425-74-6 1-nitro-7-naphthalenesulfonic acid 
• 486-54-4 1-amino-naphthalene-2,7-disulfonic acid 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 20191-62-2 8-hydroxy-naphthalene-2-sulfonic acid 

Downstream Products

• 899-76-3 8-p-toluidino-naphthalene-2-sulfonic acid 
• 6357-78-4 8-amino-5-nitro-naphthalene-2-sulfonic acid 
• 483-84-1 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid 
• 118-46-7 8-amino-2-naphthol 
• 575-38-2 1,7-Dihydroxynaphthalene 
• 20191-62-2 8-hydroxy-naphthalene-2-sulfonic acid 
• 6357-90-0 5,8-diamino-naphthalene-2-sulfonic acid 
• 607-13-6 8-anilino-1-naphthalenesulfonic acid 
• 68121-31-3 8-amino-5-phenylazo-naphthalene-2-sulfonic acid 

Relevant articles and documents

Preparation method of clean product 1, 6 and 1,7 mixed

The invention relates to a preparation method of a cleaning type product 1,6- and 1,7-Cleve's acid. The method comprises the following steps: performing sulfonation on refined naphthalene to obtain 2-naphthalene sulfonic acid, performing nitration for the formation of a mixture of 1-nitro-6-naphthalenesulfonic acid and 1-nitro-7-naphthalenesulfonic acid, performing neutralization through ammonia water, and finally performing hydrazine hydrate reduction to obtain the 1,6- and 1,7-Cleve's acid. Compared with original production process, the method provided by the invention has no generation of waste residue in the whole process, the purpose of emission reduction is achieved, and the process is more simple and convenient, and has safety and effectiveness. In addition, the overall cost of theprocess provided by the invention is lower than the overall cost of an original process.

Polyazo dye compounds having plural vinylsulfone type fiber reactive groups in one molecule

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Fiber-reactive disazo brown dye having vinylsulfone-type reactive group

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