| Identification | More | [Name]
6-Nitro-2-benzothiazolinone | [CAS]
28620-12-4 | [Synonyms]
6-NITRO-2-BENZOTHIAZOLINONE
6-NITRO-BENZOTHIAZOL-2-ONE
6-nitro-2(3H)-benzothiazolone
2(3H)-Benzothiazolone,6-nitro-(9CI)
6-Nitro-2,3-dihydro-1,3-benzothiazol-2-one | [Molecular Formula]
C7H4N2O3S | [MDL Number]
MFCD00239350 | [Molecular Weight]
196.18 | [MOL File]
28620-12-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
246 °C (dec.) (lit.) | [density ]
1.603±0.06 g/cm3(Predicted) | [Fp ]
Not applicable | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
viscous liquid | [pka]
8.78±0.20(Predicted) | [Appearance]
Light yellow to yellow Solid | [InChI]
1S/C7H4N2O3S/c10-7-8-5-2-1-4(9(11)12)3-6(5)13-7/h1-3H,(H,8,10) | [InChIKey]
QITPMSSAFSZYOP-UHFFFAOYSA-N | [SMILES]
[O-][N+](=O)c1ccc2NC(=O)Sc2c1 | [CAS DataBase Reference]
28620-12-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3
| [HS Code ]
29342000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
6-Nitro-2-benzothiazolinone may be used as a starting reagent for the synthesis of 3-alkyl-6-nitro-2-benzothiazolinones. | [General Description]
6-Nitro-2-benzothiazolinone is a 6-substituted 2-benzothiazolinone. | [Synthesis]
General procedure for the synthesis of 6-nitro-2-(3H)-benzothiazolone from 2-hydroxybenzothiazole: 3H-benzothiazol-2-one (10 g, 66 mmol) was added to 70% nitric acid (20 mL), and the reaction was stirred for 3 h at 20 °C. After completion of the reaction, the precipitate was collected by filtration and washed with deionized water. The crude product was purified by recrystallization from anhydrous ethanol. The yield of this synthesis step was 90% and the melting point of the product was 228-229 °C. It was characterized by 1H NMR (300 MHz, DMSO-d6): δ 7.28 (d, J = 8.9 Hz, 1H, H4), 8.18 (dd, J = 8.9 Hz, J = 2.4 Hz, 1H, H5), 8.65 (d, J = 2.5 Hz, 1H, H7), and 12.54 (br s, 1H, NH).13C NMR ( 75 MHz, DMSO-d6) characterization: δ 111.9 (CH), 119.6 (CH), 123.2 (CH), 125.0 (Caro), 142.5 (Caro), 142.9 (Caro), 171.0 (CO).LCMS (ESI-) analysis: calculated value of [M-H+] is 195.0; measured value is 195.0. | [References]
[1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 807 - 817
[2] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1503 - 1509
[3] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 67 - 80
[4] Chemistry of Heterocyclic Compounds, 1990, vol. 25, # 11, p. 1294 - 1296
[5] Patent: US2003/40533, 2003, A1 |
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https://www.jkchemical.com |
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Sigma-Aldrich
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https://www.sigmaaldrich.cn |
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