4-Iodo-2-nitrotoluene Chemical Properties

Melting point:

43 °C

Boiling point:

286.9±20.0 °C(Predicted)

Density 

1.883±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder to crystal

color 

Light yellow to Yellow to Orange

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

CAS DataBase Reference

41252-97-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-22

Hazard Note 

Irritant

HS Code 

2904200090

MSDS

• Language:English Provider:ALFA

4-Iodo-2-nitrotoluene Usage And Synthesis

Chemical Properties

Brown crystalline

Uses

4-Iodo-2-nitrotoluene is used to produce 3-(4-methyl-3-nitro-phenyl)-1H-indole at the temperature of 40°C.

Synthesis

Synthesis of 4-iodo-2-nitrotoluene: To an aqueous (40 mL) suspension of 4-methyl-3-nitroaniline (4.30 g, 28.26 mmol) cooled in an ice-water bath, 98% sulfuric acid (1.89 mL) was slowly added. Subsequently, sodium chloride was added to an ice-water bath to reduce the temperature to -2°C and a solution of NaNO2 (2.15 g, 31.10 mmol) in water (10 mL) was added at a rate that controlled the reaction temperature to not exceed -2°C. After addition, the mixture was stirred at -2°C for 45 minutes. The resulting diazonium salt solution was slowly added to the boiling NaI solution (12.89 g, 86 mmol) in batches (note: vigorous gas release). After addition, the reaction mixture was cooled to room temperature and extracted four times with dichloromethane (50 mL). The organic phases were combined, washed sequentially with saturated NaHCO3 solution (40 mL) and water (40 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford 4-iodo-2-nitrotoluene (6.07 g, 82% yield).1H NMR (400 MHz, CDCl3): δ 8.28 (d, 1H, J = 1.8 Hz, Ar-H), 7.81 (dd, 1H, J = 2.2, 8.1 Hz, Ar-H), 7.09 (d, 1H, J = 8.1 Hz, Ar-H), 2.55 (d, 1H, J = 8.1 Hz, Ar-H), 7.09 (d, 1H, J = 8.1 Hz, Ar-H). Ar-H), 2.55 (s, 3H, CH3).

References

[1] Patent: US9200319, 2015, B2. Location in patent: Page/Page column 57; 58
[2] Angewandte Chemie - International Edition, 2001, vol. 40, # 17, p. 3148 - 3151
[3] Chemistry - A European Journal, 2002, vol. 8, # 6, p. 1485 - 1499
[4] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 121; 122
[5] Justus Liebigs Annalen der Chemie, 1871, vol. 158, p. 337

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