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| | 5-METHYLINDOLE-3-CARBOXALDEHYDE Basic information |
| | 5-METHYLINDOLE-3-CARBOXALDEHYDE Chemical Properties |
| Melting point | 148-151 °C(lit.) | | Boiling point | 348.2±22.0 °C(Predicted) | | density | 1.226±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | pka | 15.68±0.30(Predicted) | | Appearance | Off-white to pink Solid | | InChI | 1S/C10H9NO/c1-7-2-3-10-9(4-7)8(6-12)5-11-10/h2-6,11H,1H3 | | InChIKey | ZTNQWTPWKNDRNF-UHFFFAOYSA-N | | SMILES | Cc1ccc2[nH]cc(C=O)c2c1 | | CAS DataBase Reference | 52562-50-2(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-METHYLINDOLE-3-CARBOXALDEHYDE Usage And Synthesis |
| Uses | 5-Methyl-1H-indole-3-carbaldehyde (cas# 52562-50-2) is a useful reagent for regio- and enantioselective preparation of N-alkylated indole- and pyrrole-3-carbaldehydes. | | Uses | 5-Methylindole-3-carboxaldehyde was used in the synthesis of novel flexible tripodal ligand derived from 3-methylindole and its mononuclear Zn(II),Cu(II), Ni(II), Hg(II) and Pd(II) complexes. | | Synthesis | GENERAL STEPS: Oxalyl chloride (0.3 mL) was slowly added dropwise to cooled (ice bath) N,N-dimethylformamide (DMF, 3 mL) under stirring conditions. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, a solution of 5-methylindole (4 mmol) dissolved in DMF (1.5 mL) was added slowly dropwise to the above reaction mixture. The resulting mixture was stirred and reacted at room temperature for 5 hours. Upon completion of the reaction, 2N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100 °C and maintained for 10 min. The reaction solution was cooled and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent of ethyl acetate/petroleum ether (3:1, v/v) to finally obtain the purified 5-methyl-1H-indole-3-carbaldehyde. | | References | [1] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[2] Patent: EP1932833, 2008, A1. Location in patent: Page/Page column 11; 12
[3] Chemistry - A European Journal, 2016, vol. 22, # 2, p. 716 - 723
[4] Marine Drugs, 2014, vol. 12, # 4, p. 1757 - 1772
[5] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 70 - 81 |
| | 5-METHYLINDOLE-3-CARBOXALDEHYDE Preparation Products And Raw materials |
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