2-Amino-6-nitrobenzothiazole supplier

Name
2-Amino-6-nitrobenzothiazole
EINECS 228-513-7
CAS No. 6285-57-0
Article Data76
CAS DataBase
Density 1.621 g/cm³
Solubility
Melting Point 247-249 °C(lit.)
Formula C₇H₅N₃O₂S
Boiling Point 411.7 °C at 760 mmHg
Molecular Weight 195.202
Flash Point 202.8 °C
Transport Information UN 2811 6.1/PG 3
Appearance yellow crystalline powder
Safety 26-36-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Benzothiazole,2-amino-6-nitro- (6CI,7CI,8CI);2-Amino-6-nitro-1,3-benzothiazole;6-Nitro-1,3-benzothiazol-2-ylamine;6-Nitro-2-aminobenzothiazole;6-Nitro-2-benzothiazolamine;6-Nitrobenzothiazol-2-amine;NSC 10794;NSC62341;NSC 62980;SKA 4;
PSA 112.97000
LogP 2.89110

Synthetic route

: 333-20-0
potassium thioacyanate

: 100-01-6
4-nitro-aniline

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With sodium iodide dichloride at 70℃; for 2h;	99%
Stage #1: potassium thioacyanate; 4-nitro-aniline With nano-BF3/SiO2 In acetonitrile for 0.5h; Cooling with ice; Stage #2: With bromine In acetonitrile at 0 - 20℃; for 5h;	90%
With bromine In acetic acid for 3h;	77%

: 136-95-8
2-amino-benzthiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With sulfuric acid; nitric acid 1 h, (-)10 deg C; 2 h, RT;;	97%
With nitric acid at -5 - 0℃; for 1h;	87%
With sulfuric acid; nitric acid at 5 - 20℃; for 3h;	80%
With nitric acid
With sulfuric acid; nitric acid

: 1147550-11-5
ammonium thiocyanate

: 100-01-6
4-nitro-aniline

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With bromine; acetic acid at 0 - 20℃;	68%
With bromine; acetic acid for 1h; cooling;	32%
Stage #1: ammonium thiocyanate With bromine; acetic acid at 10℃; for 0.5h; Stage #2: 4-nitro-aniline With acetic acid at 10℃; for 19h;	15%

: 3696-22-8
p-nitrophenylthiourea

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With bromine In chloroform	60%
With chloroform; bromine
With lead(II) dihydrogen orthophosphate; H2; buffer solution In methanol for 1.5h; Heating;

: 1367199-55-0
BrH*C7H5N3O2S

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With ammonium hydroxide In water Heating;
With ammonium hydroxide In water pH=11;
With ammonium hydroxide In water

: 100-01-6
4-nitro-aniline

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With ammonium thiocyanate; bromine; acetic acid
With ammonium thiocyanate; formic acid
Multi-step reaction with 2 steps 1: bromine; acetic acid / water / 0 - 10 °C 2: hydrogenchloride / water / 2 h / Reflux View Scheme

6-nitro-benzthiazolethione: 6-nitro-benzthiazolethione

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With ammonia at 160℃; im Rohr;

: 540-72-7
sodium thiocyanide

: 100-01-6
4-nitro-aniline

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With bromine; acetic acid	73%
With bromine; acetic acid
With formic acid

: 2942-06-5
6-nitrobenzo[d]thiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With hydrogenchloride; potassium hydroxide; ethanol; hydroxylamine
With potassium hydroxide; hydroxylamine hydrochloride In ethanol at 48 - 52℃;

: 2407-11-6
2-chloro-6-nitrobenzothiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With ammonium hydroxide at 150 - 160℃; unter Druck;
With ammonium hydroxide; ammonia at 140℃; unter Druck;
With ammonium hydroxide unter Druck;

: ammonium thiocyanate

: 100-01-6
4-nitro-aniline

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With bromine; acetic acid at 0 - 20℃;
With ammonia; bromine; acetic acid
With ammonia; bromine; acetic acid

: 95-16-9
1,3-Benzothiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, H2SO4 / 6 - 8 °C 2: NH2OH*HCl, KOH / ethanol / 48 - 52 °C View Scheme
Multi-step reaction with 2 steps 1: HNO3, H2SO4 / 6 - 8 °C 2: NH2OH*HCl, KOH / ethanol / 48 - 52 °C View Scheme

: 149-30-4
2-Mercaptobenzothiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O2 2: HNO3, H2SO4 / 6 - 8 °C 3: NH2OH*HCl, KOH / ethanol / 48 - 52 °C View Scheme
Multi-step reaction with 3 steps 1: H2O2 2: HNO3, H2SO4 / 6 - 8 °C 3: NH2OH*HCl, KOH / ethanol / 48 - 52 °C View Scheme

: 68310-01-0
C7H5N3O2S

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With hydrogenchloride In water for 2h; Reflux;

: 150-13-0
4-amino-benzoic acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / acetic acid / 1 h / 0 - 10 °C 2: hydrogenchloride; water / 2 h / Reflux View Scheme

: 18330-64-8
4-amino-3-thiocyanatobenzoic acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With hydrogenchloride; water for 2h; Reflux;

: 136-95-8
2-amino-benzthiazole

: 625-58-1
ethyl nitrate

: 6285-57-0
2-amino-6-nitrobenzothiazole

Conditions

Conditions	Yield
With sulfuric acid

: 136-95-8
2-amino-benzthiazole

: 625-58-1
ethyl nitrate

: 7664-93-9
sulfuric acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

...Expand

: 136-95-8
2-amino-benzthiazole

: 7697-37-2
nitric acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 6285-57-0
2-amino-6-nitrobenzothiazole

: N-(1H-imidazol-1-ylcarbonyl)-4-methoxybenzylamine

: 1334127-13-7
1-(4-methoxybenzyl)-3-(6-nitrobenzo[d]thiazol-2-yl)urea

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 22h;	100%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 98-88-4
benzoyl chloride

: 51126-54-6
N-(6-nitrobenzo[d]thiazol-2-yl)benzamide

Conditions

Conditions	Yield
With triethylamine; dmap In tetrahydrofuran for 4h; Heating;	99%
With pyridine at 20 - 60℃;	86%
With pyridine at 20 - 60℃;	86%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 5407-51-2
benzothiazole-2,6-diamine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 1125.11 Torr;	99%
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	98%
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; under 2250.23 Torr; for 2.5h;	96%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 2516-37-2
2-bromo-6-nitro-benzo[d]thiazole

Conditions

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃; Inert atmosphere;	99%
With hydrogen bromide; copper(I) bromide; sodium nitrite In water at 20℃; for 0.5h;	93%
With hydrogen bromide; copper(I) bromide; sodium nitrite In water at 20℃; for 1h;	88.4%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 116-81-4
1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid

: 1229115-40-5
1-amino-4-[(6-nitro-2-benzothiazolyl)amino]-9,10-anthraquinone-2-sulfonic acid

Conditions

Conditions	Yield
With copper; potassium carbonate; copper(II) sulfate In water at 90℃; for 4h;	98%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 3400-45-1
cyclopentanecarboxylic acid

: N-(6-nitrobenzothiazol-2-yl)cyclopentanecarboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	97%

: 16874-33-2
tetrahydro-2-furancarboxylic acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

: C12H11N3O4S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 40℃; for 6h;	97%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 874-60-2
4-methyl-benzoyl chloride

: 325979-29-1
[149a] 2-(4-Methylbenzoylamino)-6-nitrobenzothiazole

Conditions

Conditions	Yield
With 2,4-dichlorophenoxyacetic acid dimethylamine	96%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 2407-11-6
2-chloro-6-nitrobenzothiazole

Conditions

Conditions	Yield
Stage #1: 2-amino-6-nitrobenzothiazole With phosphoric acid; sodium nitrite In water at 0℃; for 1.5h; Stage #2: With copper(II) sulfate; sodium chloride In water at 0℃; for 0.5h;	95%
With tert.-butylnitrite; copper dichloride In acetonitrile at 65℃; for 1.75h;	77%
With phosphoric acid; copper(II) sulfate; sodium chloride; sodium nitrite	75%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 917-61-3
sodium isocyanate

: 111962-93-7
1-(6-nitrobenzothiazol-2-yl)urea

Conditions

Conditions	Yield
With acetic acid In water at 20℃; for 3h;	95%
With acetic acid In ethanol Heating;

: 70254-44-3
2,4-dihydroxyquinoline

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 1075-06-5
2,2-dihydroxy-1-phenyl-ethanone

: 3-(7-nitro-2-phenylbenzo[d]imidazo[2,1-b]thiazol-3-yl)quinoline-2,4-diol

Conditions

Conditions	Yield
With lemon juice at 110℃; for 0.25h; Green chemistry;	95%

...Expand

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 16063-05-1
2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one

: 3-(6-nitrobenzothiazol-2-yl)-2-(4-nitrophenyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
In pyridine Reflux;	95%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 14737-89-4
3,4-dimethoxy-trans-cinnamic acid

: 1415662-73-5
(2E)-3-(3,4-dimethoxyphenyl)-N-(6-nitro-1,3-benzothiazol-2-yl)acrylamide

Conditions

Conditions	Yield
With N,N-dimethyl-formamide; dicyclohexyl-carbodiimide In neat (no solvent) at 140℃; for 0.0333333h; Microwave irradiation;	93%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 84358-13-4
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

: tert-butyl 4-[(6-nitro-1,3-benzothiazol-2-yl)carbamoyl]piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-amino-6-nitrobenzothiazole In N,N-dimethyl-formamide at 20℃;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;	67%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: (S)-benzyl-[2-[(6-nitrobenzo[d]thiazol-2-yl)carbamoyl]pyrrolidine-1-yl]carboxylate

Conditions

Conditions	Yield
Stage #1: N-Benzyloxycarbonyl-L-proline With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: 2-amino-6-nitrobenzothiazole With dmap In dichloromethane at 20℃;	92.03%
Stage #1: N-Benzyloxycarbonyl-L-proline With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: 2-amino-6-nitrobenzothiazole With dmap In dichloromethane at 20℃;	92.03%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 108-24-7
acetic anhydride

: 80395-50-2
N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

Conditions

Conditions	Yield
With pyridine In acetone for 8h; Reflux;	92%
With pyridine at 90℃; for 4h;	79%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 14h; Inert atmosphere;	75%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 24424-99-5
di-tert-butyl dicarbonate

: 862822-06-8
(6-nitrobenzothiazol-2-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap In dichloromethane at 25℃; for 18h;	92%
With dmap In N,N-dimethyl-formamide at 90℃; for 1h;	87.5%
With dmap In N,N-dimethyl-formamide at 90℃; for 18h;	85%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 5-(isothiocyanatomethyl)isoquinoline

: 1-(isoquinolin-5-ylmethyl)-3-(6-nitrobenzo[d]thiazol-2-yl)thiourea

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	92%

: 848500-48-1
3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylic acid chloride

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 3,4-dichloro-5-methyl-N-(6-nitrobenzo[d]thiazol-2-yl)-1H-pyrrole-2-carboxamide

Conditions

Conditions	Yield
In toluene Reflux;	92%
In toluene Reflux;	82%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 383-53-9
2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone

: 7-nitro-2-(4-(trifluoromethyl)phenyl)benzo[d]imidazo[2,1-b]thiazole

Conditions

Conditions	Yield
In water; isopropyl alcohol at 100℃; under 11251.1 Torr; Microwave irradiation; Green chemistry;	92%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 20260-53-1
pyridine-3-carbonyl chloride hydrochloride

: 301332-47-8
N-(6-nitrobenzothiazol-2-yl)nicotinamide

Conditions

Conditions	Yield
With dmap; triethylamine In 1,4-dioxane for 12h; Heating / reflux;	91%
With triethylamine; dmap In 1,4-dioxane for 12h; Heating / reflux;	91%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 122-51-0
orthoformic acid triethyl ester

: 6-nitro-2-(1H-tetrazol-1-yl)benzo[d]thiazole

Conditions

Conditions	Yield
With sodium azide In neat (no solvent) at 90℃; for 0.916667h; Reagent/catalyst; Green chemistry;	91%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 1280582-84-4
C15H11BrCl2O

: 1370409-54-3
2-(2,4-dichlorophenyl)-3-(4-methylphenyl)-7-nitroimidazo[2,1-b][1,3]benzothiazole

Conditions

Conditions	Yield
In ethanol Reflux;	90.1%
Stage #1: 2-amino-6-nitrobenzothiazole; C15H11BrCl2O In ethanol Reflux; Stage #2: With phosphorus pentoxide In ethanol Reflux;	90.1%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 70-11-1
α-bromoacetophenone

: 38956-40-0
7-nitro-2-phenylbenzo[d]imidazo[2,1-b]thiazole

Conditions

Conditions	Yield
In water; isopropyl alcohol at 100℃; under 11251.1 Torr; Microwave irradiation; Green chemistry;	90%
In ethanol for 30h; Heating;
In ethanol Heating;
Stage #1: 2-amino-6-nitrobenzothiazole; α-bromoacetophenone In acetone for 24h; Stage #2: In water for 6h; Reflux;

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 86-92-0
3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

: 1-(4'-methylphenyl)-3-methyl-5-(2''-imino-6''-nitrobenzothiazole)pyrazole

Conditions

Conditions	Yield
In methanol for 0.0333333h; microwave irradiation;	90%

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 75-36-5
acetyl chloride

: 80395-50-2
N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane at 0 - 20℃;	90%
In chloroform at 0 - 5℃; for 3h;
With pyridine at 0 - 20℃; for 12h; Inert atmosphere;

: 6285-57-0
2-amino-6-nitrobenzothiazole

: 763903-09-9
2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid

: 1392442-09-9
N1-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	90%

: 499-83-2
Pyridine-2,6-dicarboxylic acid

: 6285-57-0
2-amino-6-nitrobenzothiazole

C7H5N3O2S*C7H5NO4: C7H5N3O2S*C7H5NO4

Conditions

Conditions	Yield
In ethanol for 4h; Reflux;	90%

2-Amino-6-nitrobenzothiazole Chemical Properties

6-NITRO-2-BENZOTHIAZOLAMINE(6285-57-0) is the chemical compound with the formula C₇H₅N₃O₂S. Its molar weight is 195.2g/mol.
6-NITRO-2-BENZOTHIAZOLAMINE(6285-57-0) is also named IFLAB-BB F1386-0392;LABOTEST-BB LT00454107;6-NITRO-BENZOTHIAZOL-2-YLAMINE;6-NITRO-1,3-BENZOTHIAZOL-2-AMINE;6-NITRO-2-AMINOBENZOTHIAZOLE;2-AMINO-6-NITROBENZOTHIAZOLE;6-nitro-2-benzothiazolamin.
Melting Point: 247-249 ^oC(lit.)
Flash Point: 202.8 ^oC
Boiling Point: 411.7 ^oC at 760 mmHg
Index of Refraction: 1.797
Molar Refractivity: 51.35 cm³
Molar Volume: 120.3 cm³
Polarizability: 20.35 10-24cm³
Surface Tension: 89 dyne/cm
Density: 1.621 g/cm³
Enthalpy of Vaporization: 66.42 kJ/mol
Vapour Pressure: 5.48E-07 mmHg at 25 ^oC
The chemical structure of 6-NITRO-2-BENZOTHIAZOLAMINE(6285-57-0) is

2-Amino-6-nitrobenzothiazole Uses

6-NITRO-2-BENZOTHIAZOLAMINE(6285-57-0) is used as dye intermediate and in the production of C, I disperse red 136, 154, 145, 177 and C, Z disperse violet 52.

2-Amino-6-nitrobenzothiazole Toxicity Data With Reference

mic-sat 100 µLg/plate

ENMUDM Environmental Mutagenesis. 8 (Suppl 7)(1986),1.

2-Amino-6-nitrobenzothiazole Consensus Reports

Reported in EPA TSCA Inventory.

2-Amino-6-nitrobenzothiazole Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
Hazard Codes:

Xn,Xi
Risk Statements: 20/21/22-36/37/38
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-36/37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 2
RTECS: DL0865000
HazardClass: 6.1
PackingGroup: III

Product Name

2-Amino-6-nitrobenzothiazole

Synthetic route

2-Amino-6-nitrobenzothiazole Chemical Properties

2-Amino-6-nitrobenzothiazole Uses

2-Amino-6-nitrobenzothiazole Toxicity Data With Reference

2-Amino-6-nitrobenzothiazole Consensus Reports

2-Amino-6-nitrobenzothiazole Safety Profile

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