METHYL 4-IODO-3-NITROBENZOATE

METHYL 4-IODO-3-NITROBENZOATE Property

Melting point:

103-105°C

Boiling point:

360.1±32.0 °C(Predicted)

Density 

1.904±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

Appearance

Yellow to brown Solid

Water Solubility 

Soluble in DCM 10mg/0.5mL. Insoluble in water.

Sensitive 

Light Sensitive

Safety

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

METHYL 4-IODO-3-NITROBENZOATE Chemical Properties,Usage,Production

Uses

Methyl 4-iodo-3-nitrobenzoate is used as pharmaceutical intermediate.

Synthesis

Example 1: General procedure for the preparation of methyl 4-iodo-3-nitrobenzoate using methanol/sulfuric acid 1. dissolve 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) and cool the solution to 0°C. 2. sulfuric acid (3.4 g, 34.6 mmol) was added slowly to the above cooled solution. 3. the reaction mixture was gradually warmed to room temperature and subsequently heated to reflux (about 70 °C) and maintained for 8 hours. 4. Upon completion of the reaction, the reaction mixture was cooled and neutralized to pH neutral with solid NaHCO3 and filtered to remove the resulting salt. 5. The filtrate was concentrated under pressure to give a crude product. 6. Water (30 ml) was added to the crude product and extracted with methyl tertiary butyl ether (MTBE, 30 ml x 2). 7. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and filtered. 8. The solvent was evaporated under pressure to give methyl 4-iodo-3-nitrobenzoate as a yellow solid (2.67 g, 85% yield, 98% HPLC purity).

References

[1] Dalton Transactions, 2015, vol. 44, # 5, p. 2047 - 2051
[2] Chemical Communications, 2017, vol. 53, # 55, p. 7808 - 7811
[3] Patent: US2013/172618, 2013, A1. Location in patent: Paragraph 0025
[4] Patent: WO2017/48954, 2017, A1. Location in patent: Paragraph 00095
[5] Patent: WO2005/40157, 2005, A2. Location in patent: Page/Page column 68