130-17-6

Basic information

• Product Name: 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid
• Synonyms: 2-(P-AMINOPHENYL)-6-METHYLBENZOTHIAZOLE-7-SULFONIC ACID;2-(4-AMINOPHENYL)-6-METHYL-1,3-BENZOTHIAZOLE-7-SULFONIC ACID;2-(4-AMINOPHENYL)-6-METHYL-7-BENZOTHIAZOLESULFONIC ACID;2-(4-AMINOPHENYL)-6-METHYLBENZOTHIAZOLE-7-SULPHONIC ACID;DEHYDROTHIO-P-TOLUIDINE-3-MONOSULFONIC ACID;DEHYDROTHIO-P-TOLUIDINE-3-SULFONIC ACID;DEHYDROTHIO-P-TOLUIDINESULFONIC ACID;P-(6-METHYLBENZOTHIAZOLE)ANILINE MONOSULFONIC ACID
• CAS NO: 130-17-6
• Molecular Formula: C₁₄H₁₂N₂O₃S₂
• Molecular Weight: 320.39
• EINECS: 204-979-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 130-17-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 300 °C
• Appearance: Brownish-yellow powder
• Density: 1.3833 (rough estimate)
• Refractive Index: 1.7140 (estimate)
• Storage Temp.: 2-8°C
• PKA: -0.28±0.40(Predicted)
• Water Solubility: <0.1 g/100 mL at 22℃
• CAS DataBase Reference: 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid(130-17-6)
• EPA Substance Registry System: 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid(130-17-6)

Safety Data

• Hazard Codes: Xn,C
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 130-17-6(Hazardous Substances Data)

Usage

General Description

Brownish-yellow powder.

Air & Water Reactions

Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid may emit very toxic fumes of SOx and NOx.

Fire Hazard

Flash point data for 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid are not available; however, 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid is probably combustible.

Safety Profile

Poison by intravenous route. Seealso SULFONATES. When heated to decomposition itemits very toxic fumes of SOx and NO.

InChI:InChI=1/C14H12N2O3S2/c1-8-2-7-11-12(13(8)21(17,18)19)20-14(16-11)9-3-5-10(15)6-4-9/h2-7H,15H2,1H3,(H,17,18,19)

Synthetic route

6-methyl-2-<4-amino-phenyl>-benzthiazole → 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6)

Conditions	Yield
With sulfuric acid

p-toluidine (106-49-0) → 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: iron; sodium sulfide / 8 h / 165 °C / Green chemistry; Industrial scale 2: sulfur trioxide / 2.2 h / 0 °C / Green chemistry; Industrial scale View Scheme

2-(4-aminophenyl)-6-methyl-1,3-benzothiazole (92-36-4) → 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6)

Conditions	Yield
With sulfur trioxide at 0℃; for 2.2h; Reagent/catalyst; Temperature; Green chemistry; Industrial scale;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 6-methyl-2-phenyl-benzothiazole-7-sulfonic acid

Conditions	Yield
With sodium hydroxide; sulfuric acid; sodium nitrite Erwaermen des erhaltenen Diazonium-Salzes mit Aethanol;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C14H11N3O3S2

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In water Product distribution / selectivity;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2-(4-diazophenyl)-6-methylbenzothiazole-7-sulfonic acid

Conditions	Yield
With hydrogenchloride; sodium nitrite In water

C24H22N8O12S4 (1375454-22-0) + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C52H40N14O18S8

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid With hydrogenchloride; lithium hydroxide; sodium nitrite In water at 35 - 40℃; for 125h; pH=11; Stage #2: C24H22N8O12S4 With sodium carbonate In water at 20 - 40℃; for 1.81667h; pH=7.5 - 8.5; Stage #3: With sodium chloride In water at 40℃; for 0.5h;

triisopropanolamine (122-20-3) + C14H13NO5S + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C28H22N4O8S3*2C9H21NO3

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water Cooling with ice; Stage #2: triisopropanolamine; C14H13NO5S In water

tri-isopropanolamine + 2-cyanimino-4,6-dihydroxypyrimidine + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C19H13N7O5S2*C9H21NO3

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water Cooling with ice; Stage #2: tri-isopropanolamine; 2-cyanimino-4,6-dihydroxypyrimidine In water

C15H16N2O5 + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C31H28N5O6S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 10℃; for 1.5h; pH=7; Stage #2: C15H16N2O5 With sodium carbonate In water for 3h; pH=8 - 9;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2-(4-amino-3,5-dichlorophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 50 - 60℃; for 3h;
With N-chloro-succinimide In N,N-dimethyl-formamide at 50℃; for 3h;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2-(4-amino-3,5-dibromophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 50 - 60℃;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C16H12N2O6S2

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 1 h / 55 - 65 °C / pH 8 1.2: 1 h / 55 - 65 °C / pH 6 - 8 2.1: sodium hydroxide; sodium carbonate; magnesium carbonate; potassium permanganate / water / 3 h / 65 °C / pH 8 View Scheme

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2-(4-aminophenyl)-4-sulfobenzo[d]thiazole-5-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 1 h / 55 - 65 °C / pH 8 1.2: 1 h / 55 - 65 °C / pH 6 - 8 2.1: sodium hydroxide; sodium carbonate; magnesium carbonate; potassium permanganate / water / 3 h / 65 °C / pH 8 3.1: sodium hydroxide / water / 1 h / 70 - 80 °C / pH >= 11 View Scheme

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) + acetic anhydride (108-24-7) → C16H14N2O4S2

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid; acetic anhydride With sodium hydroxide In water at 55 - 65℃; for 1h; pH=8; Stage #2: With sodium carbonate In water at 55 - 65℃; for 1h; pH=6 - 8;

cyanoacetic acid chloride (16130-58-8) + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → sodium 2-[4-(2-cyanoacetamido)phenyl]-6-methylbenzothiazole-7-sulfonate

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 6.5h; Catalytic behavior; Solvent; Green chemistry; Industrial scale;	55 g

benzoic acid ethyl ester (93-89-0) + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2-[4-(2-benzamido)phenyl]-6-methylbenzothiazole-7-sulfonic acid

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide; water at 100℃; Catalytic behavior; Solvent; Temperature; Green chemistry; Industrial scale;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C31H23N11O5S2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 1 h / 0 - 5 °C / pH 2.5 - 3.5 / Cooling with ice 2: water / 20 h / 100 °C / Cooling with ice View Scheme

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C31H22N11O5S2(1-)*Ca(2+)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 1 h / 0 - 5 °C / pH 2.5 - 3.5 / Cooling with ice 2: water / 20 h / 100 °C / Cooling with ice 3: sodium hydroxide; calcium chloride / water / 1 h / pH 9 - 10 / Cooling with ice View Scheme

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C17H11Cl2N5O3S2

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; for 1h; pH=2.5 - 3.5; Cooling with ice;

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → 2C23H13Cl2N4O5S2(1-)*Ca(2+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 3 h / 50 °C 2.1: sodium hydroxide; hydrogenchloride; sodium nitrite / water / 0.5 h / 0 - 10 °C / pH 7 2.2: 1 h / 0 - 15 °C / pH 7.5 - 10 3.1: calcium chloride; sodium hydroxide / water / 1 h / pH 9 - 10 View Scheme

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C23H14Cl2N4O5S2

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 3 h / 50 °C 2.1: sodium hydroxide; hydrogenchloride; sodium nitrite / water / 0.5 h / 0 - 10 °C / pH 7 2.2: 1 h / 0 - 15 °C / pH 7.5 - 10 View Scheme

2,4-dihydroxyquinoline (70254-44-3) + 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (130-17-6) → C23H16N4O5S2

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 10℃; for 0.5h; pH=7; Stage #2: 2,4-dihydroxyquinoline With sodium hydroxide In water at 0 - 15℃; for 1h; pH=7.5 - 10;

Upstream product

• 106-49-0 p-toluidine 
• 92-36-4 2-(4-aminophenyl)-6-methyl-1,3-benzothiazole 

Relevant articles and documents

A water-soluble benzo thiazole synthesis of dye method

The present invention discloses a water-soluble benzothiazole dye synthesis method, which comprises: mixing p-toluidine, sodium sulfide and a catalyst, carrying out a cyclization reaction to produce 2-(4-anilino)-6-methyl-benzothiazole, carrying out a sulfonation reaction on the 2-(4-anilino)-6-methyl-benzothiazole and a sulfonation agent to produce 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole, adding the 2-(4-anilino)-6-methyl-7-sulfonic-benzothiazole (III) and a sodium hydroxide aqueous solution to a solvent, adding a carbonyl-containing compound, and carrying out a reaction to obtain the water-soluble benzothiazole dye. Compared with the synthesis method in the prior art, the synthesis method of the present invention has characteristics of cheap and readily available raw materials, simple process, safety and environmental protection, and is suitable for large-scale industrial production.