| Identification | Back Directory | [Name]
methyl 2-bromobenzo[d]thiazole-6-carboxylate | [CAS]
1024583-33-2 | [Synonyms]
2-bromobenzo[d]thiazole-6-carboxylate
Methyl 2-bromobenzo[d]thiazole-6-carboxylat
methyl 2-bromobenzo[d]thiazole-6-carboxylate
2-BroMo-benzothiazole-6-carboxylic acid Methyl ester
6-Benzothiazolecarboxylic acid, 2-bromo-, methyl ester | [Molecular Formula]
C9H6BrNO2S | [MDL Number]
MFCD16660646 | [MOL File]
1024583-33-2.mol | [Molecular Weight]
272.12 |
| Chemical Properties | Back Directory | [Boiling point ]
367.2±34.0 °C(Predicted) | [density ]
1.697 | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
-1.43±0.10(Predicted) | [Appearance]
Off-white to yellow Solid | [InChI]
InChI=1S/C9H6BrNO2S/c1-13-8(12)5-2-3-6-7(4-5)14-9(10)11-6/h2-4H,1H3 | [InChIKey]
XYBYYJDNPLGJSA-UHFFFAOYSA-N | [SMILES]
S1C2=CC(C(OC)=O)=CC=C2N=C1Br |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of methyl 2-bromobenzothiazole-6-carboxylate from methyl 2-aminobenzothiazole-6-carboxylate: to a solution of methyl 2-aminobenzothiazole-6-carboxylate (1.11 g, 5 mmol) and copper(II) bromide (2.23 g, 10 mmol) in acetonitrile (50 mL) was added slowly at 0 °C tert-butyl nitrite (1.32 mL, 10 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was extracted with ethyl acetate. The organic phase was washed sequentially with saturated sodium bicarbonate solution and brine. The solvent was removed by concentration under reduced pressure and the crude product was purified by fast column chromatography (eluent: hexane/ethyl acetate, 10:1, v/v) to afford methyl 2-bromobenzothiazole-6-carboxylate. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.53 (d, 1H), 8.15 (dd, 1H), 8.01 (d, 1H), 4.42 (q, 2H), 1.42 (t, 3H). Mass spectrum (ESI) m/z: 271.9 ([M + H]+). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2324 - 2328
[2] Patent: WO2008/124393, 2008, A1. Location in patent: Page/Page column 33-34
[3] Patent: WO2018/39386, 2018, A1. Location in patent: Page/Page column 138; 139
[4] Patent: US2014/200215, 2014, A1. Location in patent: Paragraph 0984; 0986 |
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