Product Name

  • Name

    2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid

  • EINECS 204-979-7
  • CAS No. 130-17-6
  • Article Data3
  • CAS DataBase
  • Density 1.505 g/cm3
  • Solubility <0.1 g/100 mL at 22 °C in water
  • Melting Point 300 °C
  • Formula C14H12N2O3S2
  • Boiling Point
  • Molecular Weight 320.393
  • Flash Point
  • Transport Information
  • Appearance Brownish-yellow powder
  • Safety 26-36/37/39
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 130-17-6 (2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid)
  • Hazard Symbols HarmfulXn, CorrosiveC
  • Synonyms p-(6-Methyl-7-sulfobenzothiazole)aniline;2-(p-Aminophenyl)-6-methyl-7-benzothiazolesulfonic acid;Dehydrothio-p-toluidinesulfonic acid;NSC 203387;NSC 44566;7-Benzothiazolesulfonicacid, 2-(p-aminophenyl)-6-methyl- (8CI);2-(4-Aminophenyl)-6-methyl-7-benzothiazolesulfonicacid;2-(4'-Aminophenyl)-6-methylbenzothiazole-7-sulfonic acid;
  • PSA 129.90000
  • LogP 4.76260

Synthetic route

6-methyl-2-<4-amino-phenyl>-benzthiazole

6-methyl-2-<4-amino-phenyl>-benzthiazole

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

Conditions
ConditionsYield
With sulfuric acid
p-toluidine
106-49-0

p-toluidine

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

Conditions
ConditionsYield
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-methyl-1,3-benzothiazole

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

6-methyl-2-phenyl-benzothiazole-7-sulfonic acid

6-methyl-2-phenyl-benzothiazole-7-sulfonic acid

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C14H11N3O3S2

C14H11N3O3S2

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium nitrite In water Product distribution / selectivity;
2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid
130-17-6

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

2-(4-diazophenyl)-6-methylbenzothiazole-7-sulfonic acid

2-(4-diazophenyl)-6-methylbenzothiazole-7-sulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water
C24H22N8O12S4
1375454-22-0

C24H22N8O12S4

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C52H40N14O18S8

C52H40N14O18S8

Conditions
ConditionsYield
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

triisopropanolamine

C14H13NO5S

C14H13NO5S

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C28H22N4O8S3*2C9H21NO3

C28H22N4O8S3*2C9H21NO3

Conditions
ConditionsYield
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
...Expand
tri-isopropanolamine

tri-isopropanolamine

2-cyanimino-4,6-dihydroxypyrimidine

2-cyanimino-4,6-dihydroxypyrimidine

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C19H13N7O5S2*C9H21NO3

C19H13N7O5S2*C9H21NO3

Conditions
ConditionsYield
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
...Expand
C15H16N2O5

C15H16N2O5

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C31H28N5O6S2(1-)*Na(1+)

C31H28N5O6S2(1-)*Na(1+)

Conditions
ConditionsYield
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'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

2-(4-amino-3,5-dichlorophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

2-(4-amino-3,5-dichlorophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

Conditions
ConditionsYield
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'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

2-(4-amino-3,5-dibromophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

2-(4-amino-3,5-dibromophenyl)-5-methylbenzo[d]thiazole-4-sulfonic acid

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 50 - 60℃;
2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid
130-17-6

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C16H12N2O6S2

C16H12N2O6S2

Conditions
ConditionsYield
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)-6-methylbenzothiazole-7-sulphonic acid

2-(4-aminophenyl)-4-sulfobenzo[d]thiazole-5-carboxylic acid

2-(4-aminophenyl)-4-sulfobenzo[d]thiazole-5-carboxylic acid

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

acetic anhydride
108-24-7

acetic anhydride

C16H14N2O4S2

C16H14N2O4S2

Conditions
ConditionsYield
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

cyanoacetic acid chloride

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

sodium 2-[4-(2-cyanoacetamido)phenyl]-6-methylbenzothiazole-7-sulfonate

sodium 2-[4-(2-cyanoacetamido)phenyl]-6-methylbenzothiazole-7-sulfonate

Conditions
ConditionsYield
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

benzoic acid ethyl ester

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

2-[4-(2-benzamido)phenyl]-6-methylbenzothiazole-7-sulfonic acid

2-[4-(2-benzamido)phenyl]-6-methylbenzothiazole-7-sulfonic acid

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C31H23N11O5S2

C31H23N11O5S2

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C31H22N11O5S2(1-)*Ca(2+)

C31H22N11O5S2(1-)*Ca(2+)

Conditions
ConditionsYield
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

1,3,5-trichloro-2,4,6-triazine

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C17H11Cl2N5O3S2

C17H11Cl2N5O3S2

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

2C23H13Cl2N4O5S2(1-)*Ca(2+)

2C23H13Cl2N4O5S2(1-)*Ca(2+)

Conditions
ConditionsYield
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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C23H14Cl2N4O5S2

C23H14Cl2N4O5S2

Conditions
ConditionsYield
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-dihydroxyquinoline

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

2-(4'-aminophenyl)-6-methylbenzothiazole-7-sulphonic acid

C23H16N4O5S2

C23H16N4O5S2

Conditions
ConditionsYield
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;

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Chemical Properties

Molecular Formula: C14H12N2O3S2
Molar mass: 320.39 g/mol
EINECS: 204-979-7
Density: 1.505 g/cm3
Index of Refraction: 1.714
Melting point: 300 °C
Water solubility: <0.1 g/100 mL at 22 ºC
Appearance: Brownish-yellow powder
Product categories of 2-(4-Aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (CAS NO.130-17-6): Intermediates of Dyes and Pigments
Structure of 2-(4-Aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (CAS NO.130-17-6):
           
XLogP3-AA: 2.5
H-Bond Donor: 2
H-Bond Acceptor: 5
IUPAC Name: 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid
Canonical SMILES: CC1=C(C2=C(C=C1)N=C(S2)C3=CC=C(C=C3)N)S(=O)(=O)O
InChI: InChI=1S/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) 
InChIKey: KGZUHYIHYBDNLC-UHFFFAOYSA-N

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Uses

 2-(4-Aminophenyl)-6-methylbenzothiazole-7-sulphonic acid (CAS NO.130-17-6) has been used for intermediate of dyes and pigments.

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Toxicity Data With Reference

1.    

ivn-mus LD50:178 mg/kg

     CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00718 .

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Consensus Reports

Reported in EPA TSCA Inventory.

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Safety Profile

Poison by intravenous route. See also SULFONATES. When heated to decomposition it emits very toxic fumes of SOx and NOx.
 

Hazard Codes: HarmfulXnCorrosiveC
Risk Statements:
20:  Harmful by inhalation
21:  Harmful in contact with skin
22:  Harmful if swallowed 
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection

2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Specification

 2-(4-Aminophenyl)-6-methylbenzothiazole-7-sulphonic acid ,its cas register number is 130-17-6.It also can be called Dehydrothio-p-toluidinesulfonic acid ; Dehydrothiotoluidine sulfonic acid ; 2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid ; 7-Benzothiazolesulfonic acid, 2-(p-aminophenyl)-6-methyl- and 7-Benzothiazolesulfonic acid, 2-(4-aminophenyl)-6-methyl- .

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