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25150-27-0

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25150-27-0 Usage

General Description

2-AMINO-5,6-DICHLOROBENZOTHIAZOLE is a chemical compound that belongs to the benzothiazole family. It is a pale yellow solid with a molecular formula of C7H5Cl2NS and a molecular weight of 204.09 g/mol. This chemical is commonly used in the pharmaceutical and agrochemical industries as an intermediate for the synthesis of various organic compounds. It has been reported to exhibit antimicrobial and anticancer activities, making it a valuable building block in drug development. However, it should be handled and used with caution due to its toxic and irritating properties.

Check Digit Verification of cas no

The CAS Registry Mumber 25150-27-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,1,5 and 0 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 25150-27:
(7*2)+(6*5)+(5*1)+(4*5)+(3*0)+(2*2)+(1*7)=80
80 % 10 = 0
So 25150-27-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H4Cl2N2S/c8-3-1-2-4-6(5(3)9)12-7(10)11-4/h1-2H,(H2,10,11)

25150-27-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-AMINO-5,6-DICHLOROBENZOTHIAZOLE

1.2 Other means of identification

Product number -
Other names 2-amino-6,7-dichlorobenzothiazole

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:25150-27-0 SDS

25150-27-0Synthetic route

(3,4-dichloro-2-fluorophenyl)thiourea

(3,4-dichloro-2-fluorophenyl)thiourea

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
With sodium hydride In 1-methyl-pyrrolidin-2-one; mineral oil at 130℃; for 3h; Inert atmosphere;38%
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

A

2-Amino-5,6-dichlorobenzothiazole
24072-75-1

2-Amino-5,6-dichlorobenzothiazole

B

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
Stage #1: ammonium thiocyanate; m,p-dichloroaniline In acetic acid at 0℃;
Stage #2: With bromine In acetic acid at 20℃; for 1h;
A 26%
B 33%
potassium thioacyanate
333-20-0

potassium thioacyanate

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

A

2-Amino-5,6-dichlorobenzothiazole
24072-75-1

2-Amino-5,6-dichlorobenzothiazole

B

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
With bromine In acetic acid
potassium thioacyanate
333-20-0

potassium thioacyanate

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
With bromine; acetic acid at 0 - 20℃;
3,4-dichlorophenylthiourea
19250-09-0

3,4-dichlorophenylthiourea

A

2-Amino-5,6-dichlorobenzothiazole
24072-75-1

2-Amino-5,6-dichlorobenzothiazole

B

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
With sulfuric acid; ammonium bromide at 100℃; for 0.75h;
Stage #1: 3,4-dichlorophenylthiourea With sulfuric acid at 20℃; for 0.5h;
Stage #2: With bromine at 40 - 115℃;
3,4-dichloro-2-fluorobenzeneamine
886762-39-6

3,4-dichloro-2-fluorobenzeneamine

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 1.5 h / 80 °C
2: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 3 h / 130 °C / Inert atmosphere
View Scheme
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

C12H8Cl4N2S2
875895-70-8

C12H8Cl4N2S2

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol100%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

6-Amino-2,3-dichloro-benzenethiol
6647-25-2

6-Amino-2,3-dichloro-benzenethiol

Conditions
ConditionsYield
With sodium hydroxide Heating;99.5%
Multi-step reaction with 2 steps
1: 100 percent / KOH / propan-2-ol
2: dithiothreitol / dimethylformamide
View Scheme
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-benzylidene-2-phenyloxazole-5(4H)-one
842-74-0

4-benzylidene-2-phenyloxazole-5(4H)-one

5-benzylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-one
1252042-77-5

5-benzylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-one

Conditions
ConditionsYield
With pyridine Reflux;80%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

1,3,5-trichloro-2,4,6-triazine
108-77-0

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

6-chloro-N,N'-bis (6,7-dichloro-1,3-benzothiazol-2-yl)-1,3,5-triazine-2,4-diamine
1252674-95-5

6-chloro-N,N'-bis (6,7-dichloro-1,3-benzothiazol-2-yl)-1,3,5-triazine-2,4-diamine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 20℃; for 4h;79%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

C22H15NO3
297142-55-3

C22H15NO3

C29H17Cl2N3O2S
1252042-90-2

C29H17Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;78%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(3-chlorobenzylidene)-2-phenyloxazol-5(4H)-one
145509-70-2, 13289-35-5

4-(3-chlorobenzylidene)-2-phenyloxazol-5(4H)-one

C23H12Cl3N3OS
1252042-94-6

C23H12Cl3N3OS

Conditions
ConditionsYield
With pyridine Reflux;78%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(2-chlorobenzylidene)-2-phenyl-5-oxazolone
52900-69-3, 77435-90-6, 82301-55-1

4-(2-chlorobenzylidene)-2-phenyl-5-oxazolone

C23H12Cl3N3OS
1252042-92-4

C23H12Cl3N3OS

Conditions
ConditionsYield
With pyridine Reflux;78%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(2-nitrobenzylidene)-2-phenyl-5(4H)oxazolone
7621-81-0

4-(2-nitrobenzylidene)-2-phenyl-5(4H)oxazolone

C23H12Cl2N4O3S
1252042-96-8

C23H12Cl2N4O3S

Conditions
ConditionsYield
With pyridine Reflux;78%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
5429-22-1

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

C24H15Cl2N3O2S
1252042-87-7

C24H15Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;76%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one
82301-50-6, 82301-53-9, 113697-03-3

4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one

C24H15Cl2N3O2S
1252042-86-6

C24H15Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;75%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(3'-nitrobenzylidene)-2-phenyl-4-oxazolone
15601-45-3, 66949-11-9, 123990-32-9

4-(3'-nitrobenzylidene)-2-phenyl-4-oxazolone

C23H12Cl2N4O3S
1252042-99-1

C23H12Cl2N4O3S

Conditions
ConditionsYield
With pyridine Reflux;75%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone
76505-93-6

4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone

C23H13Cl2N3O2S
1252042-81-1

C23H13Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;75%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

2-phenyl-4-salicyliden-4H-oxazol-5-one
39167-74-3, 57427-90-4, 137401-65-1

2-phenyl-4-salicyliden-4H-oxazol-5-one

C23H13Cl2N3O2S
1252042-78-6

C23H13Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;72%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

C20H20N2O3
1252042-76-4

C20H20N2O3

C27H22Cl2N4O2S
1252043-06-3

C27H22Cl2N4O2S

Conditions
ConditionsYield
With pyridine Reflux;70%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one
1226-71-7, 57427-89-1, 82301-52-8

4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one

C23H13Cl2N3O2S
1252042-85-5

C23H13Cl2N3O2S

Conditions
ConditionsYield
With pyridine Reflux;70%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

(Z/E)-4-(4-chlorobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one
15601-44-2

(Z/E)-4-(4-chlorobenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one

C23H12Cl3N3OS
1252042-95-7

C23H12Cl3N3OS

Conditions
ConditionsYield
With pyridine Reflux;70%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

2-phenyl-4-(2,4,5-trimethoxy-benzylidene)-4H-oxazol-5-one
22892-39-3

2-phenyl-4-(2,4,5-trimethoxy-benzylidene)-4H-oxazol-5-one

C26H19Cl2N3O4S
1252043-03-0

C26H19Cl2N3O4S

Conditions
ConditionsYield
With pyridine Reflux;68%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

2-Phenyl-4-(3',4',5'-trimethoxybenzylidene)oxazolone
62616-09-5

2-Phenyl-4-(3',4',5'-trimethoxybenzylidene)oxazolone

C26H19Cl2N3O4S
1252043-04-1

C26H19Cl2N3O4S

Conditions
ConditionsYield
With pyridine Reflux;66%
4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
14326-80-8, 71198-75-9, 71198-76-0

4-(4-hydroxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

C24H15Cl2N3O3S
1252043-02-9

C24H15Cl2N3O3S

Conditions
ConditionsYield
With pyridine Reflux;65%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

C17H12BrNO4
339284-72-9

C17H12BrNO4

C24H14BrCl2N3O3S
1252043-05-2

C24H14BrCl2N3O3S

Conditions
ConditionsYield
With pyridine Reflux;65%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

ethyl 9,10-dichloro-7-thia-2,5-diazatricyclo[6.4.0.02,6]dodeca-1(8),3,5,9,11-pentaene-4-carboxylate

ethyl 9,10-dichloro-7-thia-2,5-diazatricyclo[6.4.0.02,6]dodeca-1(8),3,5,9,11-pentaene-4-carboxylate

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 85℃;52%
1.) THF, 4 h, 2.) THF, EtOH, reflux, 3 h; Yield given. Multistep reaction;
In N,N-dimethyl-formamide for 24h;
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

2-methyl-4-(5-nitro-2-furfurylmethyliden)-Δ2-oxazolin-5-one
16237-70-0

2-methyl-4-(5-nitro-2-furfurylmethyliden)-Δ2-oxazolin-5-one

2-acetylamino-N-(6,7-dichloro-benzothiazol-2-yl)-3-(5-nitro-furan-2-yl)-acrylamide

2-acetylamino-N-(6,7-dichloro-benzothiazol-2-yl)-3-(5-nitro-furan-2-yl)-acrylamide

Conditions
ConditionsYield
In 1,4-dioxane for 12h; Heating;48%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

4-bromoethyl acetoacetate
13176-46-0

4-bromoethyl acetoacetate

ethyl 2-{9,10-dichloro-7-thia-2,5-diazatricyclo[6.4.0.02,6]dodeca-1(8),3,5,9,11-pentaen-4-yl}acetate

ethyl 2-{9,10-dichloro-7-thia-2,5-diazatricyclo[6.4.0.02,6]dodeca-1(8),3,5,9,11-pentaen-4-yl}acetate

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 80℃; for 5h; Reflux;13%
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

8,9-dichloro-4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylic acid ethyl ester
50850-82-3

8,9-dichloro-4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
(heating);
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

3,4-dichloro-11,12-dihydro-6H-5-thia-12-aza-dibenzo[a,e]cyclooctene
875896-01-8

3,4-dichloro-11,12-dihydro-6H-5-thia-12-aza-dibenzo[a,e]cyclooctene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / KOH / propan-2-ol
2: dithiothreitol / dimethylformamide
3: dimethylformamide / 20 °C
4: LiBH4 / tetrahydrofuran / Heating
5: PPh3*Br2; imidazole / CH2Cl2 / 50 °C
View Scheme
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

[2-(6-amino-2,3-dichloro-phenylsulfanylmethyl)-phenyl]-methanol
875895-90-2

[2-(6-amino-2,3-dichloro-phenylsulfanylmethyl)-phenyl]-methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / KOH / propan-2-ol
2: dithiothreitol / dimethylformamide
3: dimethylformamide / 20 °C
4: LiBH4 / tetrahydrofuran / Heating
View Scheme
6,7-dichloro-1,3-benzothiazol-2-amine
25150-27-0

6,7-dichloro-1,3-benzothiazol-2-amine

2-(6-amino-2,3-dichloro-phenylsulfanylmethyl)-benzoic acid methyl ester
875895-78-6

2-(6-amino-2,3-dichloro-phenylsulfanylmethyl)-benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / KOH / propan-2-ol
2: dithiothreitol / dimethylformamide
3: dimethylformamide / 20 °C
View Scheme

25150-27-0Relevant articles and documents

Benzothiazole disperse dye monomer compound, synthesis method and application thereof

-

Paragraph 0076-0082, (2019/10/02)

The invention discloses a benzothiazole disperse dye monomer compound. The structure of the compound is shown as formula (I) in the specification, wherein X1 and X4 are hydrogen, halogen, nitro, methyl or methoxy independently; X2 and X3 are independently hydrogen, halogen, nitro, methyl, methoxy or cyano; X5 is hydrogen or C1-C4 alkoxy; X6 is hydrogen, C1-C4 alkyl, NHCOR1 or halogen, and R1 is C1-C4 alkyl. The invention also discloses a preparation method of the benzothiazole disperse dye monomer compound and application thereof in preparation of disperse dyes. According to the invention, a phenylthiourea compound is adopted as the starting raw material, and by means of condensation ring closure, diazotization and coupling, a disperse dye filter cake can be obtained. The obtained dispersedye has bright color, high coloring intensity, good dyeing reproducibility, and has excellent promotion performance, dye uptake, dyeing fastness, sunlight resistance and sublimation fastness.

Synthesis and antibacterial activity of a novel series of 2,3-diaryl-substituted-imidazo(2,1-b)-benzothiazole derivatives

Palkar, Mahesh,Noolvi, Malleshappa,Sankangoud, Ramappa,Maddi, Veeresh,Gadad, Andanappa,Nargund, Laxmi Venkat G.

experimental part, p. 353 - 359 (2011/07/08)

Benzothiazole and imidazole compounds are extensively studied heterocyclics due to their wide spectrum of bioactivities. Among them, the imidazo(2,1-b)-benzothiazole derivatives are pharmacologically important because of their immunostimulant, anti-inflammatory, antifungal, antimicrobial, antitumor, and other activities. In the present research work, a novel series of 2,3-diaryl-substituted imidazo(2,1-b)-benzothiazoles 13a-o have been synthesized by reaction of substituted 2-aminobenzothiazoles 1-8 and an appropriately substituted a-bromo-1-(4″-substituted)-phenyl-2-(4′- substituted)-phenyl-1-ethanones 9-12 in the presence of anhydrous acetonitrile. They were characterized by physicochemical, elemental, and spectral (IR, 1H-NMR, and Mass) data. All the synthesized compounds were screened for their in-vitro antibacterial activity against Gram-positive, Gram-negative bacteria. The investigation of antibacterial screening data revealed that most of the compounds tested have demonstrated congruent activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa as compared with the standard ampicillin. Among the series, compounds 13d, 13h, and 13m exhibited excellent an antibacterial activity profile as compared with the standard. In summary, preliminary results indicate that some of the newly synthesized title compounds exhibited promising antibacterial activities and they warrant more consideration as prospective antimicrobials.

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