4,5-DIMETHOXY-2-IODOBENZOIC ACID Chemical Properties

Melting point:

206-208°C

Boiling point:

367.9±42.0 °C(Predicted)

Density 

1.790±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.01±0.10(Predicted)

Appearance

Yellow to brown Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29163990

4,5-DIMETHOXY-2-IODOBENZOIC ACID Usage And Synthesis

Uses

4,5-Dimethoxy-2-iodobenzoic acid is an organic intermediate that can be prepared by first iodinizing 3,4-dimethoxybenzaldehyde to prepare 2-iodo-4,5-dimethoxybenzaldehyde, and then oxidizing it to obtain 4,5-dimethoxy-2-iodobenzoic acid.

Synthesis

To a solution of 3,4-dimethoxybenzaldehyde (2.00 g, 12.0 mmol) in EtOH (100 mL) was added iodine (3.65 g, 14.4 mmol) and silver sulfate (4.49 g, 14.4 mmol) under nitrogen and the mixture was stirred for 3 hours at room temperature. The solvent was removed, water was added and the mixture was extracted with DCM. The organic extract was washed with brine, dried with sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by fast chromatography using petroleum ether/ethyl acetate 2:1 (v:v) as eluent to give 2-iodo-4,5-dimethoxybenzaldehyde (2.81 g, 80%).LC-MS (ES-API); 8.52 min at room temperature; m/zC9H9IO3[M+H]+ calculated value 293.0, measured value 293.0.

At 0C. , a solution of KMnO4 (0.76 g, 4.79 mmol) in water (15 mL) was added dropwise to a stirred solution of 2-iodo-4,5-dimethoxybenzaldehyde (1.0 g, 3.42 mmol) in CH3CN (25 mL). The resulting mixture was stirred at room temperature overnight. After completion of the reaction, the pH was adjusted to <7 with 1 NHCl. The mixture was extracted with DCM, the organic layers were combined, washed with brine, dried over sodium sulfate, and evaporated to give 4,5-dimethoxy-2-iodobenzoic acid (0.89 g, 85%).

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