16582-59-5

Basic information

• Product Name: 2-Amino-4,6-dichlorobenzothiazole
• Synonyms: 2-BenzothiazolaMine, 4,6-dichloro-;2-Amino-4,6-dichlor-benzothiazol;2-AMINO-4,6-DICHLOROBENZOTHIAZOLE;2-Benzothiazolamine,4,6-dichloro-(9CI);4,6-Dichloro-1,3-benzothiazol-2-amine;4,6-Dichlorobenzo[d]thiazol-2-amine;(4,6-dichloro-1,3-benzothiazol-2-yl)amine;4,6-dichloro-1,3-benzothiazol-2-amine(SALTDATA: FREE)
• CAS NO: 16582-59-5
• Molecular Formula: C₇H₄Cl₂N₂S
• Molecular Weight: 219.09
• EINECS: 263-216-6
• Product Categories: BENZOTHIAZOLE;Thiazoles
• Mol File: 16582-59-5.mol

Chemical Properties

• Melting Point: 253-255 °C
• Boiling Point: 376.7 °C at 760 mmHg
• Flash Point: 181.6 °C
• Appearance: /
• Density: 1.654 g/cm³
• Vapor Pressure: 7.13E-06mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.50±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4,6-dichlorobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4,6-dichlorobenzothiazole(16582-59-5)
• EPA Substance Registry System: 2-Amino-4,6-dichlorobenzothiazole(16582-59-5)

Safety Data

• Hazardous Substances Data: 16582-59-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4,6-dichlorobenzothiazole is used as a reactant for the preparation of substituted 2-benzothiazolamines. These benzothiazolamine derivatives serve as sodium flux inhibitors, which play a crucial role in enhancing the anticonvulsant activity of certain medications. By modulating the sodium channels in the nervous system, these inhibitors can help in the development of drugs for the treatment of epilepsy and other seizure disorders.
Used in Chemical Synthesis:
As a versatile organic compound, 2-Amino-4,6-dichlorobenzothiazole can be utilized in the synthesis of various other chemical compounds. Its unique structure allows it to be a valuable building block for the creation of new molecules with potential applications in different fields, such as materials science, agrochemicals, and pharmaceuticals.

InChI:InChI=1/C7H4Cl2N2S/c8-3-1-4(9)6-5(2-3)12-7(10)11-6/h1-2H,(H2,10,11)

Upstream product

• 540-72-7 sodium thiocyanide 
• 554-00-7 2,4-Dichloroaniline 
• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 412923-49-0 2-bromo-4,6-dichlorobenzothiazole 
• 152874-01-6 3,5-dichloro-2-aminobenzenethiol 
• 1537865-67-0 1-Benzoyl-3-(4,6-dichlorobenzothiazol-2-yl)thiourea 
• 1537865-78-3 N-[3-(4,6-dichlorobenzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene]benzamide 
• 1537865-66-9 1-(4,6-Dichlorobenzothiazol-2-yl)-3-(2,4-dichlorobenzoyl)thiourea 
• 1537865-77-2 2,4-dichloro-N-[3-(4,6-dichlorobenzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene]benzamide 

Relevant articles and documents

Synthesis and benzodiazepine receptor binding of some 4H-pyrimido[2,1-b]benzothiazol-4-ones

Synthesis and ability to displace [3H]diazepam binding from rat brain membranes of the 3-(alkoxycarbonyl)-4H-pyrimido[2,1-b]benzothiazol-4-ones 3a-p and related compounds 10-12 are described. It has been found that some compounds bind to the benzodiazepine receptor (BZR) with potency greater than chlordiazepoxide. From a structure-affinity point of view the substitution at 6-position of pyrimido[2,1-b]benzothiazole nucleus was found conductive to higher affinity. In vitro data (GABA ratio) lend support to the fact that the most active compounds 3j, 1 might possess agonist properties at BZR.

Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g., A2-3, A3-3 and A6-3, not only possessed favorable lethality rate (50%–100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure–activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.

Design, Synthesis, and Biological Evaluation of 4-Phenoxyquinoline Derivatives Containing Benzo[d]thiazole-2-yl Urea as c-Met Kinase Inhibitors

A series of novel 4-phenoxyquinoline derivatives containing the benzo[d]thiazole-2-yl urea moiety were synthesized and evaluated for their cytotoxicity against the HT-29, MKN-45, and H460 cell lines. The structures of the target compounds were confirmed by 1H NMR and MS spectra. Most of them showed moderate to excellent potency against the three tested cell lines. Especially, compound 23 was identified a promising agent (c-Met IC50 = 17.6 nM), showing the most potent anticancer activities with IC50 values of 0.18, 0.06, and 0.01 μM against the HT-29, MKN-45, and H460 cell lines, respectively. The docking results of 23 with the c-Met kinase model 3LQ8 showed a specific binding mode between the ligand and the target protein.

Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides

A series of novel N -[3-(2-benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)- ylidene] substituted benzamides (2a-k) were efficiently synthesized by heterocyclization of the corresponding 1-(benzo[d]thiazol-2-yl)-3-aroylthioureas (1a{k). The cyclization was achieved by the reaction of α-bromoacteone produced in situ using bromine in dry acetone in the presence of triethylamine. TUeBITAK.

Substituted benzothiazols with herbicidal action

Substituted benzothiazoles I and their salts STR1 used as herbicides and for the desiccation/abscission of plants.

Substituted 2-benzothiazolamines as sodium flux inhibitors: Quantitative structure-activity relationships and anticonvulsant activity

Thirty-two aryl-substituted 2-benzothiazolamines have been tested for their ability to modulate sodium flux in rat cortical slices. A QSAR analysis, applied to these derivatives, showed a trend toward increasing potency as sodium flux inhibitors with increasing lipophilicity, decreasing size, and increasing electron withdrawal of the benzo ring substitutents. Additionally, 4- or 5-substitution of the benzo ring was found to decrease potency. The combination of increased lipophilicity, small size, and electron withdrawal severely limited which groups were tolerated on the benzo ring, thus suggesting that the optimal substitution patterns have been prepared within this series. Nine of these compounds were potent inhibitors of veratridine-induced sodium flux (NaFl). These nine compounds also proved to be anticonvulsant in the maximal electroshock (MES) assay. Fourteen additional 2-benzothiazolamines demonstrated activity in the MES screen, yet exhibited no activity in the NaFl assay. These derivatives may be interacting at the sodium channel in a manner not discernible by the flux paradigm, or they may be acting by an alternative mechanism in vivo.

Monoazo dyestuffs derived from benzothiazole

A disperse dye of the formula, STR1 wherein R1 is an alkyl group having 5 to 6 carbon atoms, R2 is an alkyl group having 5 to 6 carbon atoms, a cyano-ethyl group, R3 is a hydrogen atom or a lower alkyl, amino or phenyl group, and Y1 and Y2 represent independently a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, a cyano group, a thiocyanate group or an alkylsulfonyl group, provided that both Y1 and Y2 are not hydrogen at the same time and Y1 is located at the 4- or 5-position, which is useful for dyeing hydrophobic fibers in brilliant red to violet shade with good fastnesses.