2-HYDROXY-4-IODO-BENZALDEHYDE Chemical Properties

Melting point:

87 °C

Boiling point:

290.0±30.0 °C(Predicted)

Density 

2.039±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

7.32±0.10(Predicted)

color 

Off-White

Safety Information

HS Code 

2913000090

2-HYDROXY-4-IODO-BENZALDEHYDE Usage And Synthesis

Uses

2-hydroxy-4-iodobenzaldehyde is used in the preparation of anti-B7-H3 antibodies.

Synthesis

Step 1: Preparation of 2-hydroxy-4-iodobenzaldehyde Magnesium chloride (MgCl2, 19.5 g, 204 mmol) was added batchwise to a frozen solution of commercially available 2-iodophenol (30 g, 136 mmol) in acetonitrile (ACN) while keeping the reaction temperature below 10 °C. Paraformaldehyde (28.6 g, 954 mmol) and triethylamine (TEA, 76 mL, 545 mmol) were subsequently added and the reaction was exothermic to 15 °C. The reaction mixture was heated to 72 °C and maintained for 2 hours. Upon completion of the reaction, it was cooled to room temperature, poured into saturated aqueous ammonium chloride solution (500 mL) and extracted with ethyl acetate (2 x 150 mL). The organic phases were combined and washed sequentially with aqueous sodium bicarbonate (NaHCO3) (2 × 150 mL), aqueous 1N hydrochloric acid (HCl) (2 × 150 mL) and brine (2 × 150 mL). The organic layer was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (silica gel, 5% ethyl acetate/hexane). The target fractions were collected, combined and the solvent was removed under reduced pressure to give 2-hydroxy-4-iodobenzaldehyde (27 g, 79% yield) as a yellow solid. The salicylaldehyde derivative was of suitable purity and could be used directly in the subsequent reaction.

References

[1] Patent: WO2006/40676, 2006, A1. Location in patent: Page/Page column 51
[2] Patent: WO2004/87686, 2004, A2. Location in patent: Page 12-130
[3] Patent: WO2004/87687, 2004, A1. Location in patent: Page 12-130
[4] Patent: WO2006/40672, 2006, A1. Location in patent: Page/Page column 59

2-HYDROXY-4-IODO-BENZALDEHYDE(38170-02-4)Related Product Information

• 2-METHOXY-4-(TRIFLUOROMETHOXY)BENZALDEHYDE
• 2-Bromo-3-fluoro-6-methoxybenzaldehyde
• 2-Fluoro-3,4-dimethoxy-benzaldehyde
• 2-methoxy-3-(trifluoromethoxy)benzaldehyde
• 2-CHLORO-3,6-DIFLUOROBENZALDEHYDE
• 2,5-Dibromo-3-fluorobenzaldehyde
• 2-bromo-6-chloro-4-fluorobenzaldehyde
• Benzaldehyde, 2-bromo-6-(difluoromethoxy)-
• 2-BROMO-4-FLUORO-6-METHYLBENZALDEHYDE
• 2-Fluoro-5-methylbenzaldehyde
• 2,4-DIFLUORO-3-METHOXYBENZALDEHYDE
• 2-bromo-5-methyl-4-nitrobenzaldehyde
• 3,4-Dichloro-5-(trifluoromethyl)benzaldehyde
• 2-bromo-3-fluoro-6-hydroxybenzaldehyde
• 2-Chloro-4-trifluoroMethoxy-benzaldehyde
• Cupric acetate monohydrate
• Salicylaldoxime
• Calcium chloride