4-Chloro-2-iodo-6-nitro-phenylaMine

4-Chloro-2-iodo-6-nitro-phenylaMine Property

Melting point:

137-138 °C

Boiling point:

355.7±42.0 °C(Predicted)

Density 

2.169±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-3.20±0.25(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

4-Chloro-2-iodo-6-nitro-phenylaMine Chemical Properties,Usage,Production

Synthesis

A. Synthesis of 4-chloro-2-iodo-6-nitroaniline: adapted from the method of Leeson, P.D. et al. (J. Med. Chem. 34:1243-1252 (1991)). 4-Chloro-2-nitroaniline (2.15 g, 12.45 mmol, Aldrich, direct use) was dissolved in glacial acetic acid (16 mL) followed by iodine monochloride (2.114 g, 12.90 mmol, Aldrich). The reaction mixture was heated at 120 °C for 5 h. After completion of the reaction, it was cooled to room temperature and poured into ice water (30 g). The precipitate was collected by filtration, washed with 10% sodium sulfite solution (20 mL), and finally recrystallized by methanol to give 4-chloro-2-iodo-6-nitroaniline (1.05 g, 28% yield) as long brown needle-like crystals with a melting point of 205 °C (literature values 134-135 °C). The NMR hydrogen spectrum (1H, CDCl3) data were as follows: δ 6.660 (s, 2H); 7.906 (d, 1H, J = 2.1 Hz); 8.188 (d, 1H, J = 1.8 Hz).

References

[1] Chemistry - A European Journal, 2003, vol. 9, # 21, p. 5323 - 5331
[2] Patent: US2010/291533, 2010, A1. Location in patent: Page/Page column 57
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1243 - 1252
[4] Patent: US5514680, 1996, A
[5] Journal of the Chemical Society, 1928, p. 783