2-Iodo-4-nitroaniline Chemical Properties

Melting point:

105-109 °C (lit.)

Boiling point:

377.6±27.0 °C(Predicted)

Density 

2.278 g/cm3

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Methanol

pka

-1.18±0.10(Predicted)

form 

Solid

color 

Yellow

λmax

360nm(MeOH)(lit.)

Stability:

Light Sensitive

InChI

InChI=1S/C6H5IN2O2/c7-5-3-4(9(10)11)1-2-6(5)8/h1-3H,8H2

InChIKey

LOLSEMNGXKAZBZ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C([N+]([O-])=O)C=C1I

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

Not available

WGK Germany 

3

HS Code 

29214200

2-Iodo-4-nitroaniline Usage And Synthesis

Chemical Properties

Yellow-red cryst

Uses

2-iodo-4-nitroaniline may be used to synthesize the following:

• 2-iodo-4-nitrobenzonitrile via reaction with sodium nitrite to form a diazonium salt, which then reacts with a mixture of CuCN/KCN
• 2-iodo-p-phenylenediamine by reacting with tin(II)dihydrate in conc.HCl

Synthesis Reference(s)

Synthetic Communications, 22, p. 3215, 1992 DOI: 10.1080/00397919208021135

General Description

2-Iodo-4-nitroaniline can be synthesized via reaction of 4-nitroaniline with iodine and silver acetate.

Synthesis

General procedure for the synthesis of 2-iodo-4-nitroaniline from 4-nitroaniline: 4-nitroaniline (298.2 mg, 2.16 mmol, 1.0 eq.) was dissolved in acetonitrile (3.0 mL) at room temperature, and N-iodosuccinimide (NIS, 579.1 mg, 2.36 mmol, 1.1 eq.) and trimeshylchlorosilane ( TMSCl, 27 μL, 23.1 mg, 0.21 mmol, 0.1 equiv) and the reaction was stirred at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC) and the reaction was completed after about 20 min. Water was added to the reaction mixture and the aqueous phase was extracted three times with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and saturated aqueous sodium chloride (NaCl), dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (SiO2) with 50% ethyl acetate-hexane mixed solvent as eluent to give 545.6 mg (96% yield) of 2-iodo-4-nitroaniline as yellow crystals.

References

[1] Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 772 - 780
[2] Synthesis, 2004, # 11, p. 1869 - 1873
[3] Russian Journal of Organic Chemistry, 2016, vol. 52, # 3, p. 433 - 436
[4] Zh. Org. Khim., 2016, vol. 52, # 3, p. 433 - 436,4
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1380 - 1400

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