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| | 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Basic information |
| Product Name: | 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE | | Synonyms: | 6-CYANO-2,2-DIMETHYLCHROMENE;AKOS 91886;2,2-DIMETHYL-2H-1-BENZOPYRAN-6-CARBONITRILE;2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE;2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile 97%;6-Cyano-2,2-dimethyl-2H-chromene;6-CYANO-2,2-DIMETHYL-2H-BENZO-[B]-PYRAN;2,2-DiMethyl-6-cyanochroMene | | CAS: | 33143-29-2 | | MF: | C12H11NO | | MW: | 185.22 | | EINECS: | | | Product Categories: | Miscellaneous Reagents | | Mol File: | 33143-29-2.mol |  |
| | 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Chemical Properties |
| Melting point | 45-49 °C(lit.) | | Fp | >230 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Acetone, Chloroform, Dichloromethane, DMSO, Ethyl Acetate | | form | Solid | | color | Pale Yellow Crystalline | | CAS DataBase Reference | 33143-29-2(CAS DataBase Reference) |
| WGK Germany | 3 | | HS Code | 2932990090 |
| | 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Usage And Synthesis |
| Chemical Properties | Pale Yellow Crystalline Solid | | Uses | 6-Cyano-2,2-dimethyl-2H-benzo-[b]-pyran (cas# 33143-29-2) is a compound useful in organic synthesis. | | Uses | 2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (6-Cyano-2,2-dimethylchromene) may be used in the synthesis of 3,4-epoxy-6-cyano-2,2-dimethylchromene via epoxidation. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 37, p. 841, 1972 DOI: 10.1021/jo00971a006 | | General Description | 2,2-Dimethyl-2H-1-benzopyran-6-carbonitrile (6-Cyano-2,2-dimethyl-2H-1-benzopyran) is a substituted 2,2-dimethyl-2H-1-benzopyran. It can be synthesized by the condensation reaction between 1,1-diethoxy-3-methyl-2-butene and 4-cyanophenol in the presence of pyridine. | | Synthesis | General procedure for the synthesis of 2,2-dimethyl-6-cyano-2H coumarin from 4-((2-methylbut-3-yn-2-yl)oxy)benzonitrile: 4-((2-methylbut-3-yn-2-yl)oxy)benzonitrile (1.0 g, 5.40 mmol) was dissolved in ethylene glycol (5 mL/g of substrate), and the reaction mixture was heated to 210-215 °C,. maintained for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with water. The mixture was extracted with ether (2 x 25 mL), the organic layers were combined, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure to give a bright yellow solid. Recrystallization by petroleum ether gave 2,2-dimethyl-6-cyano-2H coumarin as a yellow powder (1.0 g, quantitative yield) with a melting point of 47-48 °C (literature value: 47 °C). IR spectrum (thin film method, cm^-1): 3054, 2985, 2226, 1605, 1487, 1421, 1369, 1265, 1212, 1148, 1128, 1107, 961, 896, 828, 739, 705. ^1H NMR (400MHz, CDCl3): δ 1.45 (s, 6H). 5.70 (d, 1H, J=11.6Hz), 6.28 (d, 1H, J=11.6Hz), 6.78 (d, 1H, J=8.4Hz), 7.24 (d, 1H, J=4.0Hz), 7.37 (dd, 1H, J=8.4Hz, 4.0Hz). ^13C NMR (100 MHz, CDCl3): δ 28.4, 77.9, 103.8, 117.2, 119.3, 120.6, 121.7, 130.1, 132.2, 133.3, 156.8. | | References | [1] Tetrahedron, 2016, vol. 72, # 51, p. 8406 - 8416
[2] Organic Process Research and Development, 2001, vol. 5, # 6, p. 636 - 645
[3] Synthesis, 1995, # 6, p. 707 - 712
[4] Journal of Medicinal Chemistry, 1983, vol. 26, # 11, p. 1582 - 1589
[5] Chemical Communications, 2011, vol. 47, # 9, p. 2586 - 2588 |
| | 2,2-DIMETHYL-2H-CHROMENE-6-CARBONITRILE Preparation Products And Raw materials |
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