131-27-1

Basic information

• Product Name: 2-Amino-4,8-naphthalenedisulfonic acid
• Synonyms: 2-Ethylamino-4,8-dinaphthalene;2-Ethylamino-4,8-dinaphthalenedisulfonicacid;3-amino-1,5-naphthalenedisulfonic;3-amino-5-naphthalenedisulfonicacid;3-aminonaphthalene-1,5-disulphonicacid;4,8-disulfo-2-naphthalamine;5-Naphthalenedisulfonicacid,3-amino-1;acidiv
• CAS NO: 131-27-1
• Molecular Formula: C₁₀H₉NO₆S₂
• Molecular Weight: 303.31
• EINECS: 205-020-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 131-27-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 205.8°C (rough estimate)
• Appearance: /
• Density: 1.6329 (rough estimate)
• Refractive Index: 1.7330 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Amino-4,8-naphthalenedisulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4,8-naphthalenedisulfonic acid(131-27-1)
• EPA Substance Registry System: 2-Amino-4,8-naphthalenedisulfonic acid(131-27-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 131-27-1(Hazardous Substances Data)

Usage

Uses

2-Amino-4,8-naphthalenedisulfonic Acid is used in green preparation method of direct blended blue D 3GL.

InChI:InChI=1/C10H9NO6S2/c11-6-4-8-7(10(5-6)19(15,16)17)2-1-3-9(8)18(12,13)14/h1-5H,11H2,(H,12,13,14)(H,15,16,17)

Synthetic route

3-nitro-naphthalene-disulfonic acid-(1.5) → 3-amino-1,5-naphthalenedisulfonic acid (131-27-1)

Conditions	Yield
With iron; acetic acid

naphthalene (91-20-3) → 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + 4-amino-naphthalene-disulfonic acid-(1.5); 8-amino-naphthalene-disulfonic acid-(1.6)

Conditions	Yield
With sulfuric acid at 30 - 40℃; anschl. Nitrieren mit konz. Salpetersaeure bei 15-20grad und Reduzieren mit Eisen und Salzsaeure;

3-nitro naphthalene-1,5-disulphonic acid (117-86-2) → 3-amino-1,5-naphthalenedisulfonic acid (131-27-1)

Conditions	Yield
With sodium sulfide; sulfuric acid In water at 45℃; for 12h; Temperature;
With iron(III) oxide; hydrazine hydrate at 70 - 80℃; for 8h;	225 g

naphthalene (91-20-3) → 3-amino-1,5-naphthalenedisulfonic acid (131-27-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 30 °C 2: nitric acid / 6 h / 25 - 30 °C 3: iron(III) oxide; hydrazine hydrate / 8 h / 70 - 80 °C View Scheme

3-amino-4-methoxyacetanilide (6375-47-9) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-(2-acetylamino-4-amino-5-methoxyphenylazo)naphthalene-1,5-disulfonic acid disodium salt

Conditions	Yield
Stage #1: 3-amino-1,5-naphthalenedisulfonic acid With sodium carbonate In water pH=6; Stage #2: With hydrogenchloride; sodium nitrite at 0 - 5℃; for 1h; pH=2; Stage #3: 3-amino-4-methoxyacetanilide In water at 20℃; pH=4 - 6; Further stages.;	91%

3-chloro-5,6-diphenyl-1,2,4-triazine (34177-11-2) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-(5,6-Diphenyl-[1,2,4]triazin-3-ylamino)-naphthalene-1,5-disulfonic acid (113258-27-8)

Conditions	Yield
With triethylamine In benzene for 5h; Heating;	75%

biphenyl-4,4'-disulfonyl chloride (3406-84-6) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3,3'-<4,4'-biphenyldiylbis(sulfonylamino)>bis(1,5-naphthalenedisulfonic acid) tetrasodium salt (130798-67-3)

Conditions	Yield
With pyridine for 5h; Heating;	56%

3-Aminophenylboronic acid (30418-59-8) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-(4-amino-2-boronophenylazo)-1,5-naphthalenedisulfonic acid disodium salt

Conditions	Yield
Stage #1: 3-amino-1,5-naphthalenedisulfonic acid With hydrogenchloride; sodium nitrite for 0.25h; cooling; Stage #2: 3-Aminophenylboronic acid With sodium hydroxide at 0 - 20℃; for 4h; Further stages.;	10%

phosgene (75-44-5) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3,3'-ureylene-bis-naphthalene-1,5-disulfonic acid

Conditions	Yield
With sodium carbonate

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-hydroxy 2-methylbenzoic acid (603-80-5)

Conditions	Yield
With sodium hydroxide at 250 - 275℃;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 2-naphthol-4-sulfonic acid (6357-85-3)

Conditions	Yield
With sulfuric acid at 170 - 185℃;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → naphthalene-1,3,5-trisulphonic acid (6654-64-4)

Conditions	Yield
durch folgeweise Diazotierung, Behandlung mit xanthogensaurem Kalium, Verseifen und Oxydation mit KMnO4;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 7-aminonaphthalene-1-sulfonic acid (86-60-2)

Conditions	Yield
With sodium amalgam

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 7-aminonaphthalene-1-sulfonic acid (86-60-2) + 3-aminonaphthalene-1-sulfonic acid (573-64-8)

Conditions	Yield
With sodium hydroxide; zinc

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 7-amino-5-hydroxy-naphthalene-1-sulfonic acid

Conditions	Yield
With potassium carbonate at 215℃; durch Verschmelzen;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 5,7-dihydroxy-naphthalene-1,3-disulfonic acid

Conditions	Yield
With sulfuric acid at 80 - 120℃; man verschmilzt die erhaltene Naphthylamintrisulfonsaeure mit Natron bei 170-180grad und erhaelt so die 3-Amino-naphthol-(1)-disulfonsaeure-(5.7); diese wird nun mit Wasser auf 210-220grad erhitzt;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + m-nitrobenzoic acid chloride (121-90-4) → 3-(3-nitro-benzoylamino)-naphthalene-1,5-disulfonic acid

Conditions	Yield
With alkali

sulfuric acid (7664-93-9) + 3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + water (7732-18-5) → 2-naphthol-4-sulfonic acid (6357-85-3)

Conditions	Yield
at 170 - 185℃; unter Druck;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + sodium amalgam → 7-aminonaphthalene-1-sulfonic acid (86-60-2)

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + zinc dust + diluted NaOH-solution → 7-aminonaphthalene-1-sulfonic acid (86-60-2) + 3-aminonaphthalene-1-sulfonic acid (573-64-8)

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + potash → 7-amino-5-hydroxy-naphthalene-1-sulfonic acid

Conditions	Yield
at 215℃;

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) + sodium amalgam → naphthalen-2-ylamine (91-59-8) + sulfur dioxide

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 5,7-dihydroxy-naphthalene-1-sulfonic acid (858464-83-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potash / 215 °C / durch Verschmelzen 2: water / 200 °C View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-methoxy-2-methylbenzoyl chloride (24487-91-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH solution / 250 - 275 °C 2: aqueous alkaline solution / anschliessend Hydrolyse 3: thionyl chloride View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 2,6-dihydroxy-1,5-dimethyl-9,10-anthraquinone (860732-72-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaOH solution / 250 - 275 °C 2: aqueous alkaline solution / anschliessend Hydrolyse 3: thionyl chloride 4: aqueous HBr View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-(3-hydroxy-2-methyl-benzoyloxy)-2-methyl-benzoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution / 250 - 275 °C 2: thionyl chloride; diethyl ether View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 2,6-diacetoxy-1,5-dimethyl-anthraquinone

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. NaOH solution / 250 - 275 °C 2: aqueous alkaline solution / anschliessend Hydrolyse 3: thionyl chloride 4: aqueous HBr 5: sulfuric acid View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-methoxy-2-methylbenzoic acid (55289-06-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution / 250 - 275 °C 2: aqueous alkaline solution / anschliessend Hydrolyse View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3,3'-(3,3'-ureylene-bis-benzoylamino)-bis-naphthalene-1,5-disulfonic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: alkali 2: iron (II)-chloride; alkali / 20 °C 3: natrium carbonate View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-(3-amino-benzoylamino)-naphthalene-1,5-disulfonic acid (157871-93-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkali 2: iron (II)-chloride; alkali / 20 °C View Scheme

3-amino-1,5-naphthalenedisulfonic acid (131-27-1) → 3-[3-(3-amino-benzoylamino)-benzoylamino]-naphthalene-1,5-disulfonic acid (157871-97-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: alkali 2: iron (II)-chloride; alkali / 20 °C 3: alkali 4: iron (II)-chloride; alkali / 25 °C View Scheme

Upstream product

• 91-20-3 naphthalene 
• 117-86-2 3-nitro naphthalene-1,5-disulphonic acid 

Downstream Products

• 130798-67-3 3,3'-<4,4'-biphenyldiylbis(sulfonylamino)>bis(1,5-naphthalenedisulfonic acid) tetrasodium salt 
• 6357-85-3 2-naphthol-4-sulfonic acid 
• 86-60-2 7-aminonaphthalene-1-sulfonic acid 
• 573-64-8 3-aminonaphthalene-1-sulfonic acid 
• 91-59-8 naphthalen-2-ylamine 
• 117-88-4 2-(4-amino-2-acetylaminophenylazo)-4,8-naphthalenedisulfonic acid 
• 68189-30-0 C₁₂H₁₁NO₇S₂ 

Relevant articles and documents

Preparation method of clean product amino C acid

The invention relates to a preparation method of clean product amino C acid. The preparation method comprises the steps that refined naphthalene is doubly sulfonated, then 1,5-naphthalene disulfonic acid is obtained, after nitration, 3-nitronaphthalene-1,5-disulfonic acid is generated, then neutralizing is conducted through liquid caustic soda, and the amino C acid is obtained through hydrazine hydrate reduction. Compared with an original production technology, no waste residue is generated in the whole technological process, the purpose of emission reduction is achieved, and the technology issimpler, more convenient and safer and has the actual effect.

Asymmetric dioxazine compounds and method for dyeing or printing fiber materials using the same

An asymmetric dioxazine compound represented by the following formula (I) in the free acid form: STR1 wherein A1 and A2 independently of one another are each sulfo, halo, alkyl or alkoxy, X1 and X2 independently of one another are each hydrogen, halo, alkyl, alkoxy or phenoxy, R1 is hydrogen or unsubstituted or substituted alkyl, R2 and R3 independently of one another are each hydrogen, alkyl, alkoxy, halo or unsubstituted or substituted amino, Z is a fiber-reactive group, m and n independently of one another are each 0 or 1, provided that mn, and L is 1 or 2. This compound is suitable for dyeing and printing cellulose fiber, natural and synthetic polyamide fibers, polyurethane fiber, leather and the like and mixed yarns thereof, to obtain dyed or printed products of a color fast to light, wetness and chlorine with superior build-up and level dyeing properties.

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