2-Amino-6-(trifluoromethylthio)benzothiazole

Base Information

• Chemical Name: 2-Amino-6-(trifluoromethylthio)benzothiazole
• CAS No.: 326-45-4
• Molecular Formula: C8H5 F3 N2 S2
• Molecular Weight: 250.2639096
• Hs Code.: 2934999090
• European Community (EC) Number: 670-802-9
• DSSTox Substance ID: DTXSID30371053
• Wikidata: Q72442880
• Pharos Ligand ID: CL24WJYBLPXW
• ChEMBL ID: CHEMBL95463
• Mol file: 326-45-4.mol

Synonyms:326-45-4;2-Amino-6-(trifluoromethylthio)benzothiazole;6-((Trifluoromethyl)thio)benzo[d]thiazol-2-amine;6-(trifluoromethylsulfanyl)-1,3-benzothiazol-2-amine;6-[(trifluoromethyl)sulfanyl]-1,3-benzothiazol-2-amine;6-Trifluoromethylsulfanyl-benzothiazol-2-ylamine;2-amino-6-(trifluoromethylsulfanyl)benzothiazole;2-amino-6-(trifluoromethylthio)-1,3-benzothiazole;2-amino-6-trifluoromethylsufanylbenzothiazole;2-amino-6-(trifluoromethylsufanyl)benzothiazole;6-(trifluoromethylthio)benzo[d]thiazol-2-amine;6-trifluoromethylthio-1,3-benzothiazol-2-amine;2-amino-6-(trifluoro-methylsufanyl)benzothiazole;CHEMBL95463;C8H5F3N2S2;SCHEMBL2245983;DTXSID30371053;BDBM168436;MFCD00665748;AKOS015854751;PS-7475;6-Trifluoromethylthio-2-benzothiazolamine;US9675591, SKA-19;2-amino-6-trifluoromethylthio-benzothiazole;CS-0135786;FT-0676115;F72591;6-trifluoromethylthio-1,3-benzothiazole-2-amine;2-amino-6-(trifluoro-methylsulfanyl)benzothiazole;A821351;F3135-0002;EUH

Chemical Property of 2-Amino-6-(trifluoromethylthio)benzothiazole

Chemical Property:

• Melting Point: 153-154 °C
• Boiling Point: 287.3±50.0 °C(Predicted)
• PKA: 2.71±0.10(Predicted)
• Flash Point: 127.6oC
• PSA: 92.45000
• Density: 1.59±0.1 g/cm3(Predicted)
• LogP: 4.07160
• Storage Temp.: 2-8°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 249.98462500
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

98%min ^*data from raw suppliers

2-Amino-6-(trifluoromethylthio)-1,3-benzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1SC(F)(F)F)SC(=N2)N

Technology Process of 2-Amino-6-(trifluoromethylthio)benzothiazole

There total 6 articles about 2-Amino-6-(trifluoromethylthio)benzothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

thioorthocarbonotrifluoridic acid 4-amino-phenyl ester (372-16-7) + potassium thioacyanate (333-20-0) → SKA-19 (326-45-4)

Guidance literature:

With bromine; acetic acid; In water; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/cmdc.201900452

Reference yield:

p-nitrophenyl trifluoromethyl sulfide (403-66-7) → SKA-19 (326-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride; zinc / methanol / Reflux

2: acetic acid; bromine / 10 - 20 °C

With bromine; ammonium chloride; acetic acid; zinc; In methanol;

DOI:10.1021/acs.jmedchem.8b02021

Reference yield:

para-nitrobenzenethiol (1849-36-1) → SKA-19 (326-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C

2: ammonium chloride; zinc / methanol / Reflux

3: acetic acid; bromine / 10 - 20 °C

With bromine; potassium carbonate; ammonium chloride; acetic acid; zinc; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.8b02021

upstream raw materials:

thioorthocarbonotrifluoridic acid 4-amino-phenyl ester

ammonium thiocyanate

potassium thioacyanate

p-nitrophenyl trifluoromethyl sulfide

Downstream raw materials:

N,N-dimethyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-aniline

2,2'-[3-trifluoromethyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-phenylazanediyl]-bis-ethanol

2,2'-[3-methyl-4-(6-trifluoromethylsulfanyl-benzothiazol-2-ylazo)-phenylazanediyl]-bis-ethanol

Refernces

• 1、 Linciano, Pasquale,Pozzi, Cecilia,Iacono, Lucia Dello,Di Pisa, Flavio,Landi, Giacomo,Bonucci, Alessio,Gul, Sheraz,Kuzikov, Maria,Ellinger, Bernhard,Witt, Gesa,Santarem, Nuno,Baptista, Catarina,Franco, Caio,Moraes, Carolina B.,Müller, Wolfgang,Wittig, Ulrike,Luciani, Rosaria,Sesenna, Antony,Quotadamo, Antonio,Ferrari, Stefania,P?hner, Ina,Cordeiro-Da-Silva, Anabela,Mangani, Stefano,Costantino, Luca,Costi, Maria Paola. "Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections". . p. 3989 - 4012. Retrieved 2019/05/06.