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

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4-Chloro-2-iodo-6-nitro-phenylaMine Basic information
Product Name:4-Chloro-2-iodo-6-nitro-phenylaMine
Synonyms:4-Chloro-2-iodo-6-nitro-phenylaMine;Benzenamine, 4-chloro-2-iodo-6-nitro-;Medetomidine Impurity 66;4-Chloro-2-iodo-6-nitroaniline
CAS:123158-75-8
MF:C6H4ClIN2O2
MW:298.47
EINECS:
Product Categories:
Mol File:123158-75-8.mol
4-Chloro-2-iodo-6-nitro-phenylaMine Structure
4-Chloro-2-iodo-6-nitro-phenylaMine Chemical Properties
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)
Safety Information
MSDS Information
4-Chloro-2-iodo-6-nitro-phenylaMine Usage And Synthesis
Synthesis
4-Chloro-2-nitroaniline

89-63-4

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

123158-75-8

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
4-Chloro-2-iodo-6-nitro-phenylaMine Preparation Products And Raw materials
Raw materials4-Chloro-2-nitroaniline-->Iodine monochloride
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