| Identification | Back Directory | [Name]
4-BROMO-ISOTHIAZOLE | [CAS]
24340-77-0 | [Synonyms]
4-BROMO-ISOTHIAZOLE
4-broMo-1,2-thiazole
ISOTHIAZOLE, 4-BROMO-
4-Bromoisothiazole USP/EP/BP
4-Bromoisothiazole≥ 95% (NMR) | [Molecular Formula]
C3H2BrNS | [MDL Number]
MFCD06657593 | [MOL File]
24340-77-0.mol | [Molecular Weight]
164.02 |
| Chemical Properties | Back Directory | [Boiling point ]
83.5±23.0 °C(Predicted) | [density ]
1.857±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [form ]
solid | [pka]
1.59±0.22(Predicted) | [color ]
Light Yellow | [InChI]
InChI=1S/C3H2BrNS/c4-3-1-5-6-2-3/h1-2H | [InChIKey]
XAGKUQWKQVTDSK-UHFFFAOYSA-N | [SMILES]
S1C=C(Br)C=N1 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Synthesis]
General procedure for the synthesis of 4-bromoisothiazole from isothiazole: Bromine (12.5 g, 78.12 mmol) was added slowly and dropwise to a solution of isothiazole (5.0 g, 58.82 mmol) in acetic acid (37 mL) over a period of 20 min at 95 °C. The reaction mixture was stirred continuously at 95 °C for 6 h and subsequently cooled to room temperature. The cooled mixture was poured into ice water (100 mL). The resulting mixture was extracted with ether (200 mL x 2). The organic phases were combined and washed with 6N sodium hydroxide solution to pH 7-8, followed by drying with anhydrous sodium sulfate and filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by distillation to give 4-bromoisothiazole as a white solid (1.5 g, 15% yield). | [References]
[1] Patent: WO2017/176961, 2017, A1. Location in patent: Paragraph 00375
[2] Journal of Medicinal Chemistry, 1968, vol. 11, # 1, p. 70 - 73 |
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