3-Iodo-4-hydroxybenzaldehyde Chemical Properties

Melting point:

128-130°C

Boiling point:

257.8±25.0 °C(Predicted)

Density 

2.039±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

3-Iodo-4-hydroxybenzaldehyde Usage And Synthesis

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

3-Iodo-4-hydroxybenzaldehyde(60032-63-5)Related Product Information

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