| Identification | Back Directory | [Name]
3-IODO-4-HYDROXYBENZALDEHYDE | [CAS]
60032-63-5 | [Synonyms]
AKOS B029221
4-Formyl-2-iodophenol
4-Hyroxy-3-iodobenzaldehyde
4-HYDRO-3-IODO-BENZALDEHYDE
4-HYDROXY-3-IODOBENZALDEHYDE
3-IODO-4-HYDROXYBENZALDEHYDE | [Molecular Formula]
C7H5IO2 | [MDL Number]
MFCD00016983 | [MOL File]
60032-63-5.mol | [Molecular Weight]
248.02 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
128-130°C | [Boiling point ]
257.8±25.0 °C(Predicted) | [density ]
2.039±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
6.33±0.18(Predicted) | [color ]
White to Pale Beige | [InChI]
InChI=1S/C7H5IO2/c8-6-3-5(4-9)1-2-7(6)10/h1-4,10H | [InChIKey]
KNQVIRRXVOTGGT-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C(O)C(I)=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
3-Iodo-4-hydroxybenzaldehyde (cas# 60032-63-5) is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of 4-hydroxy-3-iodobenzaldehyde from 4-hydroxybenzaldehyde: To a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in acetic acid (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at room temperature for 16 hours and then filtered. The filtrate was poured into water (100 mL) and ethyl acetate (50 mL) was added. The aqueous phase was separated and then extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with water (2 × 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (2.0 g, 50% yield) as a white solid, which was ready to be used without further purification.LCMS (ES-) m/z 247.1 ([M-H]-) with a retention time of 1.44 min (Method 9). | [References]
[1] Organic Preparations and Procedures International, 2002, vol. 34, # 6, p. 647 - 651
[2] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 1, p. 3 - 6
[3] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8622 - 8624
[4] Synthesis, 2010, # 9, p. 1467 - 1472
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 769 - 772 |
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