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| | 5-BroMo-7-fluoro-1-indanone Basic information |
| Product Name: | 5-BroMo-7-fluoro-1-indanone | | Synonyms: | 5-BroMo-7-fluoro-1-indanone;5-broMo-7-fluoro-2,3-dihydro-1H-inden-1-one;5-bromo-7-fluoro-2,3-dihydroinden-1-one;1H-Inden-1-one, 5-bromo-7-fluoro-2,3-dihydro-;5-Bromo-7-fluoro-1-indanone 97% | | CAS: | 1242157-14-7 | | MF: | C9H6BrFO | | MW: | 229.05 | | EINECS: | | | Product Categories: | | | Mol File: | 1242157-14-7.mol |  |
| | 5-BroMo-7-fluoro-1-indanone Chemical Properties |
| storage temp. | Sealed in dry,Room Temperature | | Appearance | Light yellow to brown Solid | | InChI | InChI=1S/C9H6BrFO/c10-6-3-5-1-2-8(12)9(5)7(11)4-6/h3-4H,1-2H2 | | InChIKey | VMPKZIKGIGAVGK-UHFFFAOYSA-N | | SMILES | C1(=O)C2=C(C=C(Br)C=C2F)CC1 |
| | 5-BroMo-7-fluoro-1-indanone Usage And Synthesis |
| Uses | 5-Bromo-7-fluoro-1-indanone is a reagent used in the synthesis of RN486, a pharmaceutical used in the treatment of Rhematoid Arthritis, via BTK inhibition. | | Synthesis | General procedure for the synthesis of 5-bromo-7-fluoro-1-indanone from 1-(2-fluoro-4-bromophenyl)-3-chloro-1-propanone: to a mixture of AlCl3 (37.5 g, 282.48 mmol) and NaCl (11 g, 188.32 mmol) was added 1-(4-bromo-2-fluorophenyl)-3-chloro-1-propanone (5 g, 18.83 mmol) and the reaction temperature was maintained at 130 °C. Subsequently, the reaction temperature was slowly increased to 180 °C and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature, poured into ice water and extracted twice with ethyl acetate (2 x 100 mL). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: 5-10% ethyl acetate/hexane) to give 2.4 g (55% yield) of 5-bromo-7-fluoro-1-indanone as a brown solid. Mass spectrum (MS): m/z 229.2 ([MH]+, IBr). | | References | [1] Patent: WO2012/101011, 2012, A2. Location in patent: Page/Page column 54
[2] Patent: US2013/18055, 2013, A1. Location in patent: Paragraph 0324-0325
[3] Patent: WO2015/949, 2015, A1. Location in patent: Page/Page column 106
[4] Patent: US2010/222325, 2010, A1. Location in patent: Page/Page column 140
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 512 - 516 |
| | 5-BroMo-7-fluoro-1-indanone Preparation Products And Raw materials |
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