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| | 3-CYCLOPENTYLACRYLONITRILE Basic information |
| Product Name: | 3-CYCLOPENTYLACRYLONITRILE | | Synonyms: | 3-Cyclopentylacrylonitrile 97%;3-CYCLOPENTYLACRYLONITRILE;3-cyyclopentylacrylonitrile;3-cyclopentylprop-2-enenitrile;3-cyclopentyl-2-Propenenitrile;(E)-3-cyclopentylprop-2-enenitrile;2-Propenenitrile,3-cyclopentyl-;3-Cyclopentylprop-2-enenitrile (mixture of isomers) | | CAS: | 591769-05-0 | | MF: | C8H11N | | MW: | 121.18 | | EINECS: | 1592732-453-0 | | Product Categories: | | | Mol File: | 591769-05-0.mol |  |
| | 3-CYCLOPENTYLACRYLONITRILE Chemical Properties |
| Boiling point | 209.0±9.0 °C(Predicted) | | density | 1.027±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | form | solid | | Appearance | Colorless to light yellow Liquid | | InChI | InChI=1S/C8H11N/c9-7-3-6-8-4-1-2-5-8/h3,6,8H,1-2,4-5H2 | | InChIKey | VMELXYJYSXXORF-UHFFFAOYSA-N | | SMILES | C(#N)C=CC1CCCC1 |
| WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2926907090 | | Storage Class | 11 - Combustible Solids |
| | 3-CYCLOPENTYLACRYLONITRILE Usage And Synthesis |
| Uses | 3-Cyclopentylacrylonitrile and its derivatives are used in the preparation of ruxolitinib intermediates and trasitinib phosphate. It is associated with diseases such as thrombocytosis, true erythrocytosis and primary myelofibrosis. | | Synthesis | Step 1. A solution of diethyl cyanomethylphosphate (39.9 mL, 0.246 mol) in THF (300 mL) was added slowly and dropwise to a solution of 1.0 M potassium tert-butoxide in THF (235 mL) at 0 °C. The ice bath was removed and the reaction mixture was gradually warmed to room temperature and subsequently cooled to 0 °C again. At this temperature, a solution of cyclopentyl formaldehyde (22.0 g, 0.224 mol) in THF (60 mL) was added slowly and dropwise. The ice bath was removed and the reaction mixture was warmed to ambient temperature and stirred continuously for 64 hours. Upon completion of the reaction, the mixture was partitioned between ether and water, and the aqueous phase was extracted three times with ether followed by two extractions with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 24.4 g (89% yield) of a mixture of (2E)- and (2Z)-3-cyclopentylacrylonitrile, which was used in the subsequent steps without further purification.1H NMR (400 MHz, CDCl3): δ 6.69 (dd, 1H, trans olefin), 6.37 (t, 1H, cis-olefin), 5.29 (dd, 1H, trans-olefin), 5.20 (d, 1H, cis-olefin), 3.07-2.95 (m, 1H, cis-product), 2.64-2.52 (m, 1H, trans-product), 1.98-1.26 (m, 16H). | | References | [1] Journal of Catalysis, 2003, vol. 218, # 1, p. 191 - 200
[2] Patent: EP2349260, 2016, B1. Location in patent: Paragraph 0111
[3] Patent: CN105418616, 2016, A. Location in patent: Paragraph 0110; 0111
[4] Patent: WO2011/31554, 2011, A2. Location in patent: Page/Page column 147-148 |
| | 3-CYCLOPENTYLACRYLONITRILE Preparation Products And Raw materials |
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