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| | 2-BROMOBENZO[B]THIOPHENE Basic information |
| Product Name: | 2-BROMOBENZO[B]THIOPHENE | | Synonyms: | 2-Bromobenzothiophene;2-Bromothianaphthene;NSC 2939;NSC 43552;NSC 9008;2-Bromobenzothiophene 97%;2-Bromobenzothiophene, >=96%;Benzo[b]thiophene, 2-broMo- | | CAS: | 5394-13-8 | | MF: | C8H5BrS | | MW: | 213.1 | | EINECS: | | | Product Categories: | | | Mol File: | 5394-13-8.mol | ![2-BROMOBENZO[B]THIOPHENE Structure](CAS/GIF/5394-13-8.gif) |
| | 2-BROMOBENZO[B]THIOPHENE Chemical Properties |
| 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. | under inert gas (nitrogen or Argon) at 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 Codes | Xn | | Risk Statements | 20/21/22-36/37/38-36-22 | | Safety Statements | 22-26-36/37/39 | | WGK Germany | 3 | | Hazard Note | Harmful | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2 |
| | 2-BROMOBENZO[B]THIOPHENE Usage And Synthesis |
| 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 |
| | 2-BROMOBENZO[B]THIOPHENE Preparation Products And Raw materials |
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