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6285-57-0 Usage

Chemical Properties

yellow crystalline powder

Uses

2-Amino-6-nitrobenzothiazole has been used:as model analyte for voltammetric determination of electrochemically reducible organic substancesin the synthesis of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide derivativesin the preparation of push-pull nonlinear optical chromophores containing thiazole and benzothiazole acceptorsas a base in dye production by diazotation reaction

General Description

Orange crystals or yellow powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Amino-6-nitrobenzothiazole is incompatible with strong oxidizing agents and strong acids.

Fire Hazard

Flash point data for 2-Amino-6-nitrobenzothiazole are not available; however, 2-Amino-6-nitrobenzothiazole is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 6285-57-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,8 and 5 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6285-57:
(6*6)+(5*2)+(4*8)+(3*5)+(2*5)+(1*7)=110
110 % 10 = 0
So 6285-57-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9)

6285-57-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (B24738)  2-Amino-6-nitrobenzothiazole, 96%   

  • 6285-57-0

  • 25g

  • 357.0CNY

  • Detail
  • Alfa Aesar

  • (B24738)  2-Amino-6-nitrobenzothiazole, 96%   

  • 6285-57-0

  • 100g

  • 848.0CNY

  • Detail
  • Aldrich

  • (190241)  2-Amino-6-nitrobenzothiazole  ≥97%

  • 6285-57-0

  • 190241-25G

  • 288.99CNY

  • Detail
  • Aldrich

  • (190241)  2-Amino-6-nitrobenzothiazole  ≥97%

  • 6285-57-0

  • 190241-100G

  • 692.64CNY

  • Detail

6285-57-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-6-nitrobenzothiazole

1.2 Other means of identification

Product number -
Other names 2-BenzothiazolaMine,6-nitro

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6285-57-0 SDS

6285-57-0Synthetic route

potassium thioacyanate
333-20-0

potassium thioacyanate

4-nitro-aniline
100-01-6

4-nitro-aniline

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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%
2-amino-benzthiazole
136-95-8

2-amino-benzthiazole

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

4-nitro-aniline
100-01-6

4-nitro-aniline

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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%
p-nitrophenylthiourea
3696-22-8

p-nitrophenylthiourea

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With bromine In chloroform60%
With chloroform; bromine
With lead(II) dihydrogen orthophosphate; H2; buffer solution In methanol for 1.5h; Heating;
BrH*C7H5N3O2S
1367199-55-0

BrH*C7H5N3O2S

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With ammonium hydroxide In water Heating;
With ammonium hydroxide In water pH=11;
With ammonium hydroxide In water
4-nitro-aniline
100-01-6

4-nitro-aniline

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With ammonia at 160℃; im Rohr;
sodium thiocyanide
540-72-7

sodium thiocyanide

4-nitro-aniline
100-01-6

4-nitro-aniline

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With bromine; acetic acid73%
With bromine; acetic acid
With formic acid
6-nitrobenzo[d]thiazole
2942-06-5

6-nitrobenzo[d]thiazole

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide; ethanol; hydroxylamine
With potassium hydroxide; hydroxylamine hydrochloride In ethanol at 48 - 52℃;
2-chloro-6-nitrobenzothiazole
2407-11-6

2-chloro-6-nitrobenzothiazole

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

2-amino-6-nitrobenzothiazole

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

ammonium thiocyanate

4-nitro-aniline
100-01-6

4-nitro-aniline

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With bromine; acetic acid at 0 - 20℃;
With ammonia; bromine; acetic acid
With ammonia; bromine; acetic acid
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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
2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
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
C7H5N3O2S
68310-01-0

C7H5N3O2S

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Reflux;
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / acetic acid / 1 h / 0 - 10 °C
2: hydrogenchloride; water / 2 h / Reflux
View Scheme
4-amino-3-thiocyanatobenzoic acid
18330-64-8

4-amino-3-thiocyanatobenzoic acid

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With hydrogenchloride; water for 2h; Reflux;
2-amino-benzthiazole
136-95-8

2-amino-benzthiazole

ethyl nitrate
625-58-1

ethyl nitrate

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

2-amino-6-nitrobenzothiazole

Conditions
ConditionsYield
With sulfuric acid
2-amino-benzthiazole
136-95-8

2-amino-benzthiazole

ethyl nitrate
625-58-1

ethyl nitrate

sulfuric acid
7664-93-9

sulfuric acid

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

2-amino-6-nitrobenzothiazole

2-amino-benzthiazole
136-95-8

2-amino-benzthiazole

nitric acid
7697-37-2

nitric acid

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

2-amino-6-nitrobenzothiazole

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

2-amino-6-nitrobenzothiazole

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

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

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

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

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 22h;100%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

benzoyl chloride
98-88-4

benzoyl chloride

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

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

Conditions
ConditionsYield
With triethylamine; dmap In tetrahydrofuran for 4h; Heating;99%
With pyridine at 20 - 60℃;86%
With pyridine at 20 - 60℃;86%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

benzothiazole-2,6-diamine

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

2-bromo-6-nitro-benzo[d]thiazole

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

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

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

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

Conditions
ConditionsYield
With copper; potassium carbonate; copper(II) sulfate In water at 90℃; for 4h;98%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

cyclopentanecarboxylic acid
3400-45-1

cyclopentanecarboxylic acid

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

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

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;97%
tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

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

2-amino-6-nitrobenzothiazole

C12H11N3O4S

C12H11N3O4S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 40℃; for 6h;97%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

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

[149a] 2-(4-Methylbenzoylamino)-6-nitrobenzothiazole

Conditions
ConditionsYield
With 2,4-dichlorophenoxyacetic acid dimethylamine96%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

2-chloro-6-nitrobenzothiazole

Conditions
ConditionsYield
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 nitrite75%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

sodium isocyanate
917-61-3

sodium isocyanate

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

1-(6-nitrobenzothiazol-2-yl)urea

Conditions
ConditionsYield
With acetic acid In water at 20℃; for 3h;95%
With acetic acid In ethanol Heating;
2,4-dihydroxyquinoline
70254-44-3

2,4-dihydroxyquinoline

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

2-amino-6-nitrobenzothiazole

2,2-dihydroxy-1-phenyl-ethanone
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

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

Conditions
ConditionsYield
With lemon juice at 110℃; for 0.25h; Green chemistry;95%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

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

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

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

Conditions
ConditionsYield
In pyridine Reflux;95%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

3,4-dimethoxy-trans-cinnamic acid

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

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

Conditions
ConditionsYield
With N,N-dimethyl-formamide; dicyclohexyl-carbodiimide In neat (no solvent) at 140℃; for 0.0333333h; Microwave irradiation;93%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

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

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

N-Benzyloxycarbonyl-L-proline

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

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

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

(6-nitrobenzothiazol-2-yl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

5-(isothiocyanatomethyl)isoquinoline

5-(isothiocyanatomethyl)isoquinoline

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

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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;92%
3,4-dichloro-5-methyl-1H-pyrrole-2-carboxylic acid chloride
848500-48-1

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

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

2-amino-6-nitrobenzothiazole

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

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

Conditions
ConditionsYield
In toluene Reflux;92%
In toluene Reflux;82%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone

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

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

Conditions
ConditionsYield
In water; isopropyl alcohol at 100℃; under 11251.1 Torr; Microwave irradiation; Green chemistry;92%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

pyridine-3-carbonyl chloride hydrochloride

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

N-(6-nitrobenzothiazol-2-yl)nicotinamide

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane for 12h; Heating / reflux;91%
With triethylamine; dmap In 1,4-dioxane for 12h; Heating / reflux;91%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

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

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

Conditions
ConditionsYield
With sodium azide In neat (no solvent) at 90℃; for 0.916667h; Reagent/catalyst; Green chemistry;91%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

C15H11BrCl2O
1280582-84-4

C15H11BrCl2O

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

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

Conditions
ConditionsYield
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%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

α-bromoacetophenone
70-11-1

α-bromoacetophenone

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

7-nitro-2-phenylbenzo[d]imidazo[2,1-b]thiazole

Conditions
ConditionsYield
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;
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one

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

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

Conditions
ConditionsYield
In methanol for 0.0333333h; microwave irradiation;90%
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
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;
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

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

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

N1-(6-nitro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide
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
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;90%
Pyridine-2,6-dicarboxylic acid
499-83-2

Pyridine-2,6-dicarboxylic acid

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

2-amino-6-nitrobenzothiazole

C7H5N3O2S*C7H5NO4

C7H5N3O2S*C7H5NO4

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

6285-57-0Relevant articles and documents

Synthesis of Some New 3-(2'-Benzothiazolyl)-4(3H)-quinazolinones as Antifungal Agents

Lakhan, Ram,Ral, Babban J.

, p. 501 - 502 (1986)

Five new 2-methyl-3--4(3H)-quinazolinones have been synthesized.Three of them were tested for their antifungal activity against agricultural fungi by the food poison technique and the activity was compared with that of Dithan M-45.

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen

supporting information, (2021/09/09)

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone

Shulga,Simurova,Shulga

, p. 364 - 368 (2021/04/13)

Abstract: The condensation of 2-amino-1,3-thiazolium perchlorates and their benzo analogs with trifluoro-acetyl-acetone in acetic acid afforded the corresponding [1,3]thiazolo[3,2-a]pyrimidinium, pyrimido[2,1-b][1,3]benzothiazolium, and naphtho[2′,1′:4,5][1,3]thiazolo[3,2-a]pyrimidinium salts as a single isomer in which the trifluoromethyl group is located in the γ-position with respect to the bridgehead nitrogen atom. The structure of the synthesized compounds was confirmed by 1H NMR spectra and elemental analyses.

Synthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors

Acar ?evik, Ulviye,Osmaniye, Derya,Sa?lik, Begüm N.,Levent, Serkan,K. ?avu?o?lu, Betül,Karaduman, Abdullah B.,D. ?zkay, ümide,?zkay, Yusuf,Kaplancikli, Zafer A.,Turan, Gülhan

, p. 2225 - 2233 (2020/03/04)

Monoamine oxidases (MAO) are enzymes that catalyze the oxidative deamination of monoamines such as dopamine, noradrenaline, adrenaline, and serotonin. Recent studies have shown that numerous benzothiazole derivatives exhibit hMAO inhibitory activity in the micromolar concentration range. In this study, a novel series of benzothiazole-thiadiazole (5a-5l) was synthesized and characterized their chemical structures by 1H-NMR, 13C-NMR, and Mass spectroscopy. These compounds were evaluated as inhibitors for types A and B MAO enzymes. Compounds 5f and 5l were the most active derivatives in the series with an IC50 values of 0.107 ± 0.003 and 0.128 ± 0.004, respectively. Furthermore, cytotoxicity of compounds 5f and 5l were investigated and found as non-cytotoxic.

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