| Identification | More | [Name]
2-Amino-6-fluorobenzothiazole | [CAS]
348-40-3 | [Synonyms]
2-AMINO-6-FLUOROBENZOTHIAZOLE
6-FLUORO-1,3-BENZOTHIAZOL-2-AMINE
6-FLUORO-2-BENZOTHIAZOLAMINE
6-FLUOROBENZO[D]THIAZOL-2-AMINE
6-FLUORO-BENZOTHIAZOL-2-YLAMINE
AKOS B034895
AKOS BB-8275
ASISCHEM Y86622
OTAVA-BB BB7110950332
TIMTEC-BB SBB000158
2-Amino-6-fluorobenzo-1,3-thiazole
2-Amino-6-Fluorolbenzothiazole
2-Amino-6-fluorobenzo-1,3-thiazole 99%
2-Amino-6-fluorobenzo-1,3-thiazole99%
2-Benzothiazolamine,6-fluoro-(9CI) | [EINECS(EC#)]
609-034-6 | [Molecular Formula]
C7H5FN2S | [MDL Number]
MFCD00013336 | [Molecular Weight]
168.19 | [MOL File]
348-40-3.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to tan crystalline powder | [Melting point ]
183-185 °C (lit.) | [Boiling point ]
312.0±34.0 °C(Predicted) | [density ]
1.3490 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
3.77±0.10(Predicted) | [color ]
Off-white to tan | [InChI]
InChI=1S/C7H5FN2S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H2,9,10) | [InChIKey]
CJLUXPZQUXVJNF-UHFFFAOYSA-N | [SMILES]
S1C2=CC(F)=CC=C2N=C1N | [CAS DataBase Reference]
348-40-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29342000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [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. | [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. | [Definition]
ChEBI: 6-Fluoro-1,3-benzothiazol-2-amine is a member of benzothiazoles. | [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.), |
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