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| | 2-Benzofurancarboxaldehyde Basic information |
| | 2-Benzofurancarboxaldehyde Chemical Properties |
| Melting point | 9-9.5 °C | | Boiling point | 135 °C18 mm Hg(lit.) | | density | 1.206 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.633(lit.) | | FEMA | 3128 | 2-BENZOFURANCARBOXALDEHYDE | | Fp | >230 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Liquid | | Specific Gravity | 1.206 | | color | Clear yellow to brown | | Odor | at 100.00 %. bitter almond | | Odor Type | fruity | | Water Solubility | Not miscible or difficult to mix with water. | | Sensitive | Air Sensitive | | JECFA Number | 751 | | BRN | 2910 | | InChI | 1S/C9H6O2/c10-6-8-5-7-3-1-2-4-9(7)11-8/h1-6H | | InChIKey | ADDZHRRCUWNSCS-UHFFFAOYSA-N | | SMILES | O=Cc1cc2ccccc2o1 | | LogP | 2.09 | | CAS DataBase Reference | 4265-16-1(CAS DataBase Reference) | | NIST Chemistry Reference | Benzofuran-2-carboxaldehyde(4265-16-1) | | EPA Substance Registry System | 2-Benzofurancarboxaldehyde (4265-16-1) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29329990 | | Storage Class | 10 - Combustible liquids |
| | 2-Benzofurancarboxaldehyde Usage And Synthesis |
| Chemical Properties | 2-Formyl benzofuran has a bitter almond odor. | | Chemical Properties | Colorless to light yellow liqui | | Uses | Benzo[b]furan-2-carboxaldehyde is used for the synthesis of isoxazolines. | | Uses | 2-Benzofurancarboxaldehyde may be used in the preparation of (E)-3-(benzofuran-2′-ylmethylidene)-1-methyl-2-indolinone and 1-(benzofuran-2-yl)methanol. | | Definition | ChEBI: 2-Benzofurancarboxaldehyde is a member of benzofurans. | | Preparation | By the Gattermann process; also from coumaryloyl cyanide. | | General Description | 2-Benzofurancarboxaldehyde, also known as benzo[b]-2-furfural, is an α,β-unsaturated aldehyde. | | Synthesis | General procedure for the synthesis of benzo[b]furan-2-carbaldehyde from 2,3-benzofuran and N,N-dimethylformamide: Triclosan (4.73 mL, 50.79 mmol) was slowly added to a solution of N,N-dimethylformamide (6.56 mL, 84.75 mmol) under conditions of keeping the temperature lower than 40 °C. Subsequently, 2,3-benzofuran (2.00 g, 16.93 mmol) was added dropwise to the reaction mixture over a period of 15 min under the same temperature conditions. The reaction mixture was heated up to 80 °C for 24 hours. After completion of the reaction, the mixture was carefully poured into ice water and neutralized with sodium hydroxide solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to afford benzo[b]furan-2-carbaldehyde (2.27 g, 90% yield) as a brown oil.1H NMR (400 MHz, CDCl3): δ 9.83 (1H, s, CHO), 7.75-7.70 (1H, m, H-4 ), 7.56-7.54 (2H, m, H-6,7), 7.46 (1H, s, H-3), 7.32-7.28 (1H, m, H-5).13C NMR (100 MHz, CDCl3): δ 179.63 (CHO), 156.03 (C-7a), 152.52 (C-2), 129.07 (C-3a) , 126.51 (C-6), 124.05 (C-5), 123.58 (C-4), 117.93 (C-3), 112.44 (C-7). | | References | [1] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
[2] Organic Letters, 2012, vol. 14, # 3, p. 844 - 847
[3] Letters in Drug Design and Discovery, 2014, vol. 11, # 8, p. 975 - 984
[4] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270
[5] Patent: WO2016/114816, 2016, A1. Location in patent: Paragraph 0331 |
| | 2-Benzofurancarboxaldehyde Preparation Products And Raw materials |
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