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| | 2-Chloro-6-nitrobenzaldehyde Basic information |
| | 2-Chloro-6-nitrobenzaldehyde Chemical Properties |
| Melting point | 69-71 °C(lit.) | | Boiling point | 298.8±25.0 °C(Predicted) | | density | 1.485±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | powder to crystal | | color | White to Yellow to Orange | | InChI | InChI=1S/C7H4ClNO3/c8-6-2-1-3-7(9(11)12)5(6)4-10/h1-4H | | InChIKey | RZDOUWDCYULHJX-UHFFFAOYSA-N | | SMILES | C(=O)C1=C([N+]([O-])=O)C=CC=C1Cl | | CAS DataBase Reference | 6361-22-4(CAS DataBase Reference) |
| | 2-Chloro-6-nitrobenzaldehyde Usage And Synthesis |
| Uses | 2-Chloro-6-nitrobenzaldehyde is mainly used in organic synthesis as an intermediate for dyes and other fine chemicals. | | Synthesis | This embodiment relates to the synthesis of 2-chloro-6-nitrobenzaldehyde: To a stirred solution of 2-chloro-6-nitrotoluene (18.53 g, 108.0 mmol) in anhydrous N,N-dimethylformamide (240 mL) was added N,N-dimethylformamide dimethyl acetal (39.5 g, 44.0 mL, 331.0 mmol). After the mixture was heated at 140 °C for 16 h, the dark red solution was cooled to 0 °C and slowly added to a rapidly stirred solution of sodium periodate (83.0 g, 388.0 mmol) in water (291 mL) through a cannula over a 1 h period. The reaction flask was washed with N,N-dimethylformamide (77 mL) at 0 °C and the washings were added to the sodium periodate mixture. The reaction mixture was stirred at 0°C for 2 hours and then slowly warmed to room temperature. After continued stirring for 6 hours, the orange solution was filtered and rinsed with toluene/ethyl acetate (1:1, 200 mL). The filtrate was washed sequentially with water (3 x 150 mL) and saturated aqueous sodium chloride solution (3 x 150 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to give a dark red oil, which precipitated as a solid upon addition of hexane (40 mL). The solid was recrystallized by toluene to afford the target product 2-chloro-6-nitrobenzaldehyde (17.23 g, 92.88 mmol, 86% yield).1H NMR (400 MHz, CDCl3) δ 10.42 (s, 1H), 8.01 (dd, J=1.0, 8.2 Hz, 1H), 7.79 (dd, J=1.0, 8.1 Hz, 1H ), 7.65 (t, J=8.1Hz, 1H); 13C NMR (100MHz, CDCl3) δ 188.6, 148.4, 138.6, 132.9, 132.4, 123.4, 121.9. | | References | [1] Patent: WO2008/156656, 2008, A2. Location in patent: Page/Page column 46; 177 |
| | 2-Chloro-6-nitrobenzaldehyde Preparation Products And Raw materials |
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