118-03-6

Basic information

• Product Name: 2-Amino-3,6,8-naphthalenetrisulfonic acid
• Synonyms: 2-Amino-3,6,8-naphthalenetrisulfonic acid;K-ACID;7-aminonaphthalene-1,3,6-trisulfonic acid;2-R amino acid;2-NAPHTHYLAMINE-3,6,8-TRISULFONIC ACID (AMINO K ACID);7-Amino-1,3,6-naphthalenesulfonic Acid;7-azanylnaphthalene-1,3,6-trisulfonic acid;.beta.-Naphthylamine-3,6,8-trisulfonicacid
• CAS NO: 118-03-6
• Molecular Formula: C₁₀H₉NO₉S₃
• Molecular Weight: 383.37
• EINECS: 204-229-9
• Product Categories: Intermediates of Dyes and Pigments;Organic acids
• Mol File: 118-03-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 702.53℃[at 101 325 Pa]
• Flash Point: >230°F
• Appearance: /
• Density: 1.7995 (rough estimate)
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: 2-8°C
• PKA: -1.27±0.40(Predicted)
• Water Solubility: 1000g/L at 25℃
• CAS DataBase Reference: 2-Amino-3,6,8-naphthalenetrisulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3,6,8-naphthalenetrisulfonic acid(118-03-6)
• EPA Substance Registry System: 2-Amino-3,6,8-naphthalenetrisulfonic acid(118-03-6)

Safety Data

• Hazardous Substances Data: 118-03-6(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H9NO9S3/c11-8-4-7-5(2-10(8)23(18,19)20)1-6(21(12,13)14)3-9(7)22(15,16)17/h1-4H,11H2,(H,12,13,14)(H,15,16,17)(H,18,19,20)

Synthetic route

1-nitronaphthalene-3,6,8-trisulfonic acid → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
With sulfuric acid at 50℃; for 6.89h; electrochemical reduction;	98.1%

7-hydroxy-naphthalene-1,3,6-trisulfonic acid (6259-66-1) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
With ammonia

7-sulfoamino-naphthalene-1,3-disulfonic acid → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
With sulfuric acid at 120 - 130℃;

8-nitronaphthalene-1,3,6-trisulphonic acid (38267-31-1) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
With ammonia unter Druck;

7-hydroxy-naphthalene-1,3,6-trisulfonic acid (6259-66-1) + ammonia (7664-41-7) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

sulfuric acid (7664-93-9) + 7-sulfoamino-naphthalene-1,3-disulfonic acid → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
at 120 - 130℃;

8-nitronaphthalene-1,3,6-trisulphonic acid (38267-31-1) + ammonia (7664-41-7) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
at 100℃; unter Druck;

β-naphthol (135-19-3) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 40 - 60 °C 2: potassium chloride; ammonia; ammonium hydrogen sulfite / water / 130 °C 3: sulfuric acid / 130 °C / Inert atmosphere View Scheme

2-aminonaphthalene-6,8-disulfonate (86-65-7) → 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6)

Conditions	Yield
With sulfuric acid at 130℃; Temperature; Inert atmosphere;	195.3 g

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 1-amino-3-ureidobenzene (25711-72-2) + 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C20H14Cl2N8O7S3

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite In water for 1h; Stage #2: 1-amino-3-ureidobenzene With sodium carbonate In water at 0 - 5℃; for 2h; pH=6 - 6.5; Stage #3: 1,3,5-trichloro-2,4,6-triazine In water at 0 - 35℃; for 3h; pH=6 - 6.5;	82%

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + Cresidine (120-71-8) → C18H17N3O10S3 (101309-08-4)

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With lithium hydroxide In water pH=7 - 8; Stage #2: With hydrogenchloride; sodium nitrite In water at 0 - 10℃; for 1h; Stage #3: Cresidine With pyridine In water; acetone at 0 - 25℃;	66%
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 1h; Stage #2: Cresidine With hydrogenchloride; sodium carbonate In water at 10 - 30℃; pH=3;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4)

Conditions	Yield
With alkali at 220 - 260℃;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → naphthalene-1,3,6,7-tetrasulfonic acid

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

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → 3,6,8-trisulfo-naphthalene-2-diazonium-betaine

Conditions	Yield
Diazotization;

4-(2-Iodo-ethyl)-naphthalen-1-ol (38661-32-4) + 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → 7-[1-Hydroxy-4-(2-iodo-ethyl)-naphthalen-2-ylazo]-naphthalene-1,3,6-trisulfonic acid (41017-52-1)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) /BRN= 2364430/, aq. NaOH; Multistep reaction;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + alkali → 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4)

Conditions	Yield
at 220 - 260℃;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + alkali → 7-amino-1.3-or 1.6-dioxy-naphthalene-sulfonic acid-(6 or 3)

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → 8-hydroxy-3,6-disulfo-naphthalene-2-diazonium-betaine (34043-07-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkali / 220 - 260 °C 2: Diazotization View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C10H7N2O9S3(1+)*Cl(1-) (1426257-63-7)

3-amino-4-methoxyacetanilide (6375-47-9) + 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + 8-anilino-1-naphthalenesulfonate (82-75-7) → C29H24N6O14S4 (939374-04-6)

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With hydrogenchloride; sodium nitrite In water at 10 - 25℃; Stage #2: 3-amino-4-methoxyacetanilide With sodium carbonate In water at 15 - 25℃; pH=5.5; Stage #3: 8-anilino-1-naphthalenesulfonate With hydrogenchloride; sodium hydroxide; sodium nitrite more than 3 stages;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) + m-acetamide aniline (102-28-3) → 2-(4-amino-2-acetylaminophenylazo)-3,6,8-naphthalenetrisulfonic acid (93679-74-4)

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid Stage #2: m-acetamide aniline

1-amino-3-ureidobenzene (25711-72-2) + 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C17H15N5O10S3 (28566-82-7)

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With sodium carbonate In water at 0℃; Stage #2: With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 0.5h; Stage #3: 1-amino-3-ureidobenzene With sodium carbonate In water for 0.5h; pH=5 - 6;
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With sodium carbonate In water at 0℃; Stage #2: With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 0.5h; Stage #3: 1-amino-3-ureidobenzene With sodium carbonate In water for 0.5h; pH=5 - 6;
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With sodium nitrite In water at 0 - 2℃; for 0.166667h; Stage #2: In water at 5 - 8℃; for 1.16667h; Acidic aqueous solution; Stage #3: 1-amino-3-ureidobenzene With sodium carbonate In water at 8 - 10℃; for 1.33333 - 1.5h; pH=4.0;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C26H25N5O11S3 (101309-09-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium hydroxide / water / pH 7 - 8 1.2: 1 h / 0 - 10 °C 1.3: 0 - 25 °C 2.1: hydrogenchloride; sodium nitrite / water / 1.5 h / 0 - 5 °C 2.2: 0 - 25 °C / pH 6 View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C45H38N10O17S5

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hydroxide / water / pH 7 - 8 1.2: 1 h / 0 - 10 °C 1.3: 0 - 25 °C 2.1: hydrogenchloride; sodium nitrite / water / 1.5 h / 0 - 5 °C 2.2: 0 - 25 °C / pH 6 3.1: hydrogenchloride; sodium nitrite / 1.5 h / 0 - 5 °C 3.2: 2.25 h / 20 - 35 °C 3.3: 70 °C / pH 4.5 View Scheme

3-amino-4-methoxyacetanilide (6375-47-9) + 7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C19H18N4O11S3 (108094-73-1)

Conditions	Yield
Stage #1: 7-aminonaphthalene-1,3,6-trisulfonic acid With hydrogenchloride; sodium nitrite In water at 8 - 15℃; for 1h; Cooling with ice; Stage #2: 3-amino-4-methoxyacetanilide With sodium hydroxide In water at 20℃; for 2h; pH=5 - 5.5;

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C29H24N6O14S4 (939374-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 8 - 15 °C / Cooling with ice 1.2: 2 h / 20 °C / pH 5 - 5.5 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 5 - 10 °C 2.2: 2 h / 10 - 15 °C / pH 6 - 6.5 View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C32H23Cl2N9O14S4 (1025062-43-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 8 - 15 °C / Cooling with ice 1.2: 2 h / 20 °C / pH 5 - 5.5 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 5 - 10 °C 2.2: 2 h / 10 - 15 °C / pH 6 - 6.5 3.1: sodium carbonate / water / 1 h / 0 - 15 °C / pH 6 - 7 View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C32H25ClN10O14S4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 8 - 15 °C / Cooling with ice 1.2: 2 h / 20 °C / pH 5 - 5.5 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 5 - 10 °C 2.2: 2 h / 10 - 15 °C / pH 6 - 6.5 3.1: sodium carbonate / water / 1 h / 0 - 15 °C / pH 6 - 7 4.1: ammonia / water / 1 h / 40 - 45 °C View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C38H30N11O16S4(1+) (1403244-25-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 8 - 15 °C / Cooling with ice 1.2: 2 h / 20 °C / pH 5 - 5.5 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 5 - 10 °C 2.2: 2 h / 10 - 15 °C / pH 6 - 6.5 3.1: sodium carbonate / water / 1 h / 0 - 15 °C / pH 6 - 7 4.1: ammonia / water / 1 h / 40 - 45 °C 5.1: water / 5 h / 80 - 90 °C View Scheme

7-aminonaphthalene-1,3,6-trisulfonic acid (118-03-6) → C39H31ClN10O14S4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 8 - 15 °C / Cooling with ice 1.2: 2 h / 20 °C / pH 5 - 5.5 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 5 - 10 °C 2.2: 2 h / 10 - 15 °C / pH 6 - 6.5 3.1: sodium carbonate / water / 1 h / 0 - 15 °C / pH 6 - 7 4.1: water / 1 h / 40 - 45 °C View Scheme

Upstream product

• 6259-66-1 7-hydroxy-naphthalene-1,3,6-trisulfonic acid 
• 7664-93-9 sulfuric acid 
• 38267-31-1 8-nitronaphthalene-1,3,6-trisulphonic acid 
• 7664-41-7 ammonia 
• 86-65-7 2-aminonaphthalene-6,8-disulfonate 
• 135-19-3 β-naphthol 

Downstream Products

• 90-40-4 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid 

Relevant articles and documents

Production method of K acid

A production method of a K acid comprises the following steps: 1, mixing 2-naphthol (I) with 92-98% sulfuric acid, introducing a gas, and carrying out a primary sulfonation reaction to obtain a compound (II); 2, reacting the compound (II) with a potassium salt and an ammonium salt, and carrying out an ammonification reaction and sulfuric acid acidifying to obtain a compound (III); and 3, mixing the compound (III) with 95-98% sulfuric acid, introducing a gas, and carrying out a secondary sulfonation reaction to obtain a compound (IV) that is the K acid. The chemical equation of the method is shown in the description. The method effectively increases the utilization rate of sulfuric acid in the sulfonation process, greatly reduces the production amount of waste sulfuric acid and even industrial sulfates, avoids production operating inconvenience brought by use of 20% nicotinic acid and 65% nicotinic acid, improves the operability of the process, and also has the advantages of small sulfuric acid use amount, low production cost, high product quality and small environmental pollution.

Reactive dye having both monochlorotriazinyl and vinylsulfone type reactive groups

A novel reactive monoazo dye, capable of giving cellulose fiber materials a deep orange to scarlet color and superior in build-up and chlorine fastness properties, represented by a free acid of the formula, STR1 wherein R1 is hydrogen, methyl or ethyl; R2 is an alkyl having 1 to 4 carbons that is either unsubstituted or substituted with hydroxy, cyano, alkoxy, halogen, carboxy, alkoxycarbonyl or sulfonic acid; Z is hydrogen or sulfonic acid; A is phenylene and is either unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, bromine and sulfonic acid, or natphthylene that is either unsubstituted or substituted with sulfonic acid; X is --SO2 CH=CH2 or --SO2 CH2 CH2 Y in which Y is a group that is splittable by alkalis; and m is an integer of 1 to 3.

Bisazo brown reactive dye

A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.