Structure
Crystals of 2-amino-6-fluoro-1,3-benzothiazole, C7H5FN2S, have an amphiphilic layer-like structure. Each amino substituent donates two protons to hydrogen bonds and accepts one. The ring N atoms accept one proton. The F atoms are not involved in any hydrogen bonds.
Chemical Properties
off-white to tan crystalline powder
Uses
2-Amino-6-fluorobenzothiazole is a useful research chemical. An intermediate for the synthesis of benzothiazoles and aminobenzothiazoles with antimicrobial activity.
Definition
ChEBI: 6-Fluoro-1,3-benzothiazol-2-amine is a member of benzothiazoles.
Application
2-Amino-6-fluorobenzothiazole (AFBT) can be used for:
(1) Interaction of AFBT with β-cyclodextrin (β-CDx) in aqueous and solid state. The proton transfer behaviour of AFBT in aqueous and β-CDx solutions was studied.
(2) Spectroscopic studies. Fourier transform infrared spectroscopy (4000-400 cm-1) and Fourier transform Raman spectroscopy (4000-100 cm-1) measurements were carried out on AFBT to investigate the effect of fluorine and amino groups on the backbone pattern and proton chemical shifts.
Synthesis
GENERAL METHOD: 4-Fluoroaniline (0.1 mol) and potassium thiocyanate (0.4 mol) were dissolved in glacial acetic acid (40 mL) and the mixture was cooled. Bromine (0.04 mol) mixed with glacial acetic acid (24 mL) was added slowly through a dropping funnel, controlling the rate of addition to maintain the reaction temperature below 5-6°C. After the bromine was added, the reaction mixture continued to be stirred at low temperature for 2 hours. The reaction mixture was allowed to stand overnight, during which time an orange-yellow precipitate precipitated and settled to the bottom. Water was added to the mixture and the resulting slurry was heated on a steam bath at 85°C for 20 minutes, followed by filtration while hot. The filtrate was cooled and neutralized with aqueous ammonia solution to pH 6. The precipitated yellow precipitate was collected, washed with water and recrystallized by benzene to give 2-amino-6-fluorobenzothiazole crystals. The method is also applicable for the synthesis of 1,3-benzothiazol-2-amines and their derivatives 1-3 [21,22].
References
[1] Organic Letters, 2017, vol. 19, # 21, p. 5836 - 5839
[2] Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 64 - 76
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8599 - 8607
[4] Russian Journal of Applied Chemistry, 2015, vol. 88, # 12, p. 2065 - 2073
[5] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.),
