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| | 4-Cyanotetrahydro-4H-pyran Basic information |
| Product Name: | 4-Cyanotetrahydro-4H-pyran | | Synonyms: | 4-CYANOTETRAHYDRO-4H-PYRAN;4-Cyanotetrahydropyran;tetrahydro-2H-pyran-4-carbonitrile(SALTDATA: FREE);Tetrahydro-pyran-4-carbonitrile;4-cyanotetrahydropiran;oxane-4-carbonitrile;2H-Pyran-4-carbonitrile, tetrahydro-;4-Cyanotetrahydro-4H-pyran manufacturer | | CAS: | 4295-99-2 | | MF: | C6H9NO | | MW: | 111.14 | | EINECS: | | | Product Categories: | | | Mol File: | 4295-99-2.mol |  |
| | 4-Cyanotetrahydro-4H-pyran Chemical Properties |
| Boiling point | 82-83 °C(Press: 10 Torr) | | density | 1.0343 g/cm3 | | refractive index | 1.4521 | | storage temp. | 2-8°C | | Appearance | Colorless to light yellow Liquid | | InChI | InChI=1S/C6H9NO/c7-5-6-1-3-8-4-2-6/h6H,1-4H2 | | InChIKey | RLZJFTOYCVIYLE-UHFFFAOYSA-N | | SMILES | C1OCCC(C#N)C1 |
| RIDADR | UN2811 | | HazardClass | IRRITANT | | HS Code | 2932990090 |
| | 4-Cyanotetrahydro-4H-pyran Usage And Synthesis |
| Uses | Tetrahydro-2H-Pyran-4-Carbonitrile is used in preparation of substituted Amide compounds as farnesoid X receptor modulators. | | Synthesis | The general procedure for the synthesis of 4-cyanotetrahydropyran from tetrahydropyran-4-carboxamide was as follows: thionyl chloride (10.0 mL, 137 mmol) was slowly added to tetrahydropyran-4-carboxamide (3.0 g, 23 mmol), and the reaction mixture was stirred under reflux for 4 hr. Upon completion of the reaction, the mixture was carefully decanted onto ice and the pH was adjusted with 50% sodium hydroxide solution to 14. Subsequently, the aqueous phase was extracted with ethyl acetate (3 x 50 mL), the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give a light yellow oily product (2.4 g, 94% yield) which did not require further purification. The structure of the product was confirmed by the following characterization data: IR (νmax, cm-1 ): 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011; 1H NMR (500 MHz, CDCl3): δ 3.91 (2H, ddd, J = 11.9, 6.3, 3.6 Hz, 2 × 3.6 Hz, 2 × 3.6 Hz, 2 × 3.9, 6.3, 3.6 Hz, 2 × 3.6 Hz). 3.6 Hz, 2×2-HA), 3.61 (2H, ddd, J = 11.9, 7.8, 3.3 Hz, 2×2-HB), 2.91-2.85 (1H, m, 4-H), 1.99-1.92 (2H, m, 2×3-HA), 1.91-1.84 (2H, m, 2×3-HB); 13C NMR (75 MHz, CDCl3): δ 121.2, 65.6, 28.9, 25.3; HRMS (ESI+): calculated value C6H10NO ([M+H]+): 112.0756, measured value: 112.0754, Δ -1.8 ppm. | | References | [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 11, p. 2629 - 2635
[2] Patent: US2007/111984, 2007, A1. Location in patent: Page/Page column 45
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 370
[4] Patent: US2009/253679, 2009, A1. Location in patent: Page/Page column 54-55 |
| | 4-Cyanotetrahydro-4H-pyran Preparation Products And Raw materials |
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