Product Name

  • Name

    4-Amino-5-chloro-2,1,3-benzothiadiazole

  • EINECS 1308068-626-2
  • CAS No. 30536-19-7
  • Article Data2
  • CAS DataBase
  • Density 1.632 g/cm3
  • Solubility
  • Melting Point 89 °C
  • Formula C6H4ClN3S
  • Boiling Point 316.4 °C at 760 mmHg
  • Molecular Weight 185.637
  • Flash Point 145.1 °C
  • Transport Information
  • Appearance white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 30536-19-7 (4-Amino-5-chloro-2,1,3-benzothiadiazole)
  • Hazard Symbols
  • Synonyms 5-Chloro-4-amino-2,1,3-benzothiadiazole;
  • PSA 80.04000
  • LogP 2.50810

Synthetic route

5-chloro-4-nito-2,1,3-benzothiadiazole
2274-89-7

5-chloro-4-nito-2,1,3-benzothiadiazole

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

Conditions
ConditionsYield
With iron
With iron; acetic acid In methanol
5-chloro-2,1,3-benzothiadiazole
2207-32-1

5-chloro-2,1,3-benzothiadiazole

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated HNO3; concentrated H2SO4
2: iron
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid
2: iron; acetic acid / methanol
View Scheme
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

5-chloro-N-(N-acetyl-4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine

5-chloro-N-(N-acetyl-4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine

Conditions
ConditionsYield
With trichlorophosphate In acetone at 50 - 55℃; for 20h; Temperature; Solvent;93.6%
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

potassium ethyl xanthogenate
140-89-6

potassium ethyl xanthogenate

methyl iodide
74-88-4

methyl iodide

C8H5N3S3

C8H5N3S3

Conditions
ConditionsYield
Stage #1: 4-amino-5-chloro-2,1,3-benzothiadiazole; potassium ethyl xanthogenate In N,N-dimethyl-formamide for 18h; Inert atmosphere; Reflux;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;		91.5%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

2-chloro-2-imidazoline hydrochloride
54255-14-0

2-chloro-2-imidazoline hydrochloride

tizanidine
51322-75-9

tizanidine

Conditions
ConditionsYield
With pyridine In iso-butanol at 65 - 70℃; for 8h; Temperature; Solvent; Reagent/catalyst;90.5%
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

acetic acid
64-19-7

acetic acid

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine acetate

tizanidine acetate

Conditions
ConditionsYield
In isopropyl alcohol at -10 - 90℃; for 27h; Solvent; Temperature;88.5%
...Expand
LACTIC ACID
849585-22-4

LACTIC ACID

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine 2-hydroxypropionic acid salt

tizanidine 2-hydroxypropionic acid salt

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol at -5 - 90℃; for 46h;88.3%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

hexanoic acid
142-62-1

hexanoic acid

tizanidine hexanoate

tizanidine hexanoate

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide at 0 - 80℃; for 29h;87.5%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

malic acid
617-48-1

malic acid

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine malate

tizanidine malate

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol at 85 - 90℃; for 32.5h;87.5%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

acetic acid
64-19-7

acetic acid

methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate
60546-77-2

methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate

tizanidine acetate

tizanidine acetate

Conditions
ConditionsYield
In isopropyl alcohol at -5 - 95℃; for 28h;87%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

oxalic acid
144-62-7

oxalic acid

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine oxalate

tizanidine oxalate

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 0 - 70℃; for 31h;86.9%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

malonic acid
141-82-2

malonic acid

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine malonate

tizanidine malonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol at -10 - 90℃; for 38h; Solvent; Temperature;86.8%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

3-oxapentanoic acid
627-03-2

3-oxapentanoic acid

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine ethoxyacetate

tizanidine ethoxyacetate

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at -5 - 70℃; for 24h;86.5%
...Expand
glycolic Acid
79-14-1

glycolic Acid

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

tizanidine glycolate

tizanidine glycolate

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol at 5 - 90℃; for 41h;86.2%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

citric acid
77-92-9

citric acid

tizanidine citrate

tizanidine citrate

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide at -5 - 80℃; for 40h;86.1%
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N-acetyl-2-ethylthio-2-imidazoline
61076-80-0

N-acetyl-2-ethylthio-2-imidazoline

butyric acid
107-92-6

butyric acid

tizanidine butanoate

tizanidine butanoate

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide at -5 - 90℃; for 38h;86%
...Expand
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine hydrochloride
64461-82-1, 74113-36-3

tizanidine hydrochloride

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h;
Stage #2: With methanol for 4h; Reflux;
Stage #3: With hydrogenchloride In ethanol at 20℃; for 1h;		85%
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

sodium sulfate anhydride

sodium sulfate anhydride

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine
51322-75-9

tizanidine

Conditions
ConditionsYield
With trichlorophosphate In methanol; sodium hydroxide; water73%
...Expand
1-acetylimidazolidin-2-one
5391-39-9

1-acetylimidazolidin-2-one

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

tizanidine
51322-75-9

tizanidine

Conditions
ConditionsYield
Stage #1: 1-acetylimidazolidin-2-one; 4-amino-5-chloro-2,1,3-benzothiadiazole With trichlorophosphate at 60 - 65℃; for 36h;
Stage #2: With methanol; sodium hydroxide for 4h; Reflux;		70%
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

8H-pyrrolo[2',3':3,4]benzo[1,2-c][1,2,5]thiadiazole-7-carboxylic acid
96450-32-7

8H-pyrrolo[2',3':3,4]benzo[1,2-c][1,2,5]thiadiazole-7-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate; magnesium sulfate; acetic acid; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl acetamide at 140℃; for 14h;67%
N,N,N,N,N,N-hexamethylphosphoric triamide
680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

formic acid
64-18-6

formic acid

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C9H9ClN4S

C9H9ClN4S

Conditions
ConditionsYield
at 220 - 230℃; for 4h; Yield given;
...Expand
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

C9H9ClN4S

C9H9ClN4S

Conditions
ConditionsYield
With trichlorophosphate In benzene Yield given;
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

dichloroamine

dichloroamine

5,7-dichloro-benzo[1,2,5]thiadiazol-4-ylamine
16407-86-6

5,7-dichloro-benzo[1,2,5]thiadiazol-4-ylamine

4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

ethyl bromoacetate
105-36-2

ethyl bromoacetate

C10H10ClN3O2S

C10H10ClN3O2S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h;
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C8H6ClN3O2S

C8H6ClN3O2S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 120 °C
2: lithium hydroxide; water / tetrahydrofuran
View Scheme
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C17H22ClN5O3S

C17H22ClN5O3S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 120 °C
2: lithium hydroxide; water / tetrahydrofuran
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol
View Scheme
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C12H14ClN5OS

C12H14ClN5OS

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 120 °C
2: lithium hydroxide; water / tetrahydrofuran
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol
4: hydrogenchloride / methanol
View Scheme
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C15H16ClN5O2S

C15H16ClN5O2S

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 120 °C
2: lithium hydroxide; water / tetrahydrofuran
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol
4: hydrogenchloride / methanol
5: triethylamine / dichloromethane
View Scheme
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

7-hydrazino-thiazolo[4',5':3,4]benzo[1,2-c][1,2,5]thiadiazole
91982-37-5

7-hydrazino-thiazolo[4',5':3,4]benzo[1,2-c][1,2,5]thiadiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 18 h / Inert atmosphere; Reflux
1.2: 1 h / 0 °C / Inert atmosphere
2.1: hydrazine hydrate / propan-1-ol / 8 h / Inert atmosphere; Reflux
View Scheme
4-amino-5-chloro-2,1,3-benzothiadiazole
30536-19-7

4-amino-5-chloro-2,1,3-benzothiadiazole

C14H9N5O2S2

C14H9N5O2S2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide / 18 h / Inert atmosphere; Reflux
1.2: 1 h / 0 °C / Inert atmosphere
2.1: hydrazine hydrate / propan-1-ol / 8 h / Inert atmosphere; Reflux
3.1: propan-1-ol / 2 h / Inert atmosphere; Reflux
View Scheme

4-Amino-5-chloro-2,1,3-benzothiadiazole Specification

The 2,1,3-Benzothiadiazol-4-amine,5-chloro-, with the CAS registry number 30536-19-7, is also known as 4-Amino-5-chloropiazthiole. It belongs to the product categories of Aromatics Compounds; Aromatics; Heterocycles; Tizanidine Hydrochloride. This chemical's molecular formula is C6H4ClN3S and molecular weight is 185.63. Its IUPAC name is called 5-chloro-2,1,3-benzothiadiazol-4-amine. You should keep container tightly sealed which should be stored in a cool, dry place. What's more, you should ensure that workplaces have good ventilation or exhaust. This chemical is white solid.

Physical properties of 2,1,3-Benzothiadiazol-4-amine,5-chloro-: (1)ACD/LogP: 1.67 ; (2)#H bond acceptors: 3; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 1; (5)Index of Refraction: 1.781; (6)Molar Refractivity: 47.79 cm3; (7)Molar Volume: 113.7 cm3; (8)Surface Tension: 84 dyne/cm; (9)Density: 1.632 g/cm3; (10)Flash Point: 145.1 °C; (11)Enthalpy of Vaporization: 55.77 kJ/mol; (12)Boiling Point: 316.4 °C at 760 mmHg; (13)Vapour Pressure: 0.000412 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC2=NSN=C2C(=C1Cl)N
(2)InChI: InChI=1S/C6H4ClN3S/c7-3-1-2-4-6(5(3)8)10-11-9-4/h1-2H,8H2
(3)InChIKey: MURNIACGGUSMAP-UHFFFAOYSA-N

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