| Identification | Back Directory | [Name]
2-BROMOBENZO[B]THIOPHENE | [CAS]
5394-13-8 | [Synonyms]
NSC 2939
NSC 9008
NSC 43552
2-Bromothianaphthene
2-Bromobenzothiophene
2-BROMOBENZO[B]THIOPHENE
2-BROMO-1-BENZOTHIOPHENE
2-Bromobenzothiophene 97%
Benzo[b]thiophene, 2-broMo-
2-Bromobenzothiophene, >=96%
2-Bromobenzo[b]thiophene 97%
2-BROMOBENZO[B]THIOPHENE ISO 9001：2015 REACH | [Molecular Formula]
C8H5BrS | [MDL Number]
MFCD08435846 | [MOL File]
5394-13-8.mol | [Molecular Weight]
213.09 |
| Chemical Properties | Back Directory | [Melting point ]
44.5-45℃ | [Boiling point ]
284.7±13.0 °C(Predicted) | [density ]
1.649±0.06 g/cm3(Predicted) | [Fp ]
>110℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
solid | [color ]
White | [InChI]
InChI=1S/C8H5BrS/c9-8-5-6-3-1-2-4-7(6)10-8/h1-5H | [InChIKey]
WIFMYMXKTAVDSQ-UHFFFAOYSA-N | [SMILES]
C1(Br)SC2=CC=CC=C2C=1 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
2-Bromobenzo[b]thiophene is used in the stereoselective preparation of halogenated benzoxazines via enantioselective halocyclization of o-anilidostyrenes using chiral anion phase-transfer catalysts. | [Synthesis]
To a solution of benzo[b]thiophene (2.0 g, 15 mmol) in tetrahydrofuran (20 mL) was slowly added n-butyllithium (2.5 M hexane solution, 12 mL, 30 mmol) dropwise at -70 °C and under nitrogen protection. The reaction mixture was stirred continuously at this temperature for 30 minutes. Subsequently, N-bromosuccinimide (5.3 g, 30 mmol) was added and the reaction system was slowly warmed from -70 °C to room temperature over 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (20 mL) followed by extraction with ethyl acetate (3 x 30 mL). The organic phases were combined, concentrated in vacuum, and the residue was purified by silica gel column chromatography [eluent: petroleum ether/ethyl acetate = 100:1] to afford 2-bromobenzothiophene (0.50 g, 16% yield) as a white solid. | [References]
[1] Patent: WO2006/56418, 2006, A2. Location in patent: Page/Page column 68-69
[2] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2542 - 2547,6
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 3034 - 3038
[4] Patent: WO2017/69980, 2017, A1. Location in patent: Paragraph 00274; 00275
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 664 |
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