3-Chloro-2-iodoaniline
3-Chloro-2-iodoaniline
CAS: 70237-25-1
Molecular Formula: C6H5ClIN
3-Chloro-2-iodoaniline - Names and Identifiers
| Name | 3-Chloro-2-iodoaniline |
| Synonyms | 3-chloro-2-iodoaniline 3-Chloro-2-iodoaniline 2-Iodo-3-chloroaniline 3-Chloro-2-iodobenzenaMine 3-CHLORO-2-IODO-PHENYLAMINE Benzenamine, 3-chloro-2-iodo- benzenamine, 3-chloro-2-iodo- 3-3-Chloro-2-iodoanilineChloro-2-iodoaniline |
| CAS | 70237-25-1 |
| InChI | InChI=1/C6H5ClIN/c7-4-2-1-3-5(9)6(4)8/h1-3H,9H2 |
3-Chloro-2-iodoaniline - Physico-chemical Properties
| Molecular Formula | C6H5ClIN |
| Molar Mass | 253.47 |
| Density | 2.015 |
| Boling Point | 304℃ |
| Flash Point | 137℃ |
| Vapor Presure | 0.000925mmHg at 25°C |
| pKa | 1.48±0.10(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
| Refractive Index | 1.694 |
3-Chloro-2-iodoaniline - Reference Information
| introduction | 3-chloro-2-iodoaniline is an organic intermediate, which can be prepared from 2-chloro-6-nitroaniline first, and then diazotized to prepare 1-chloro-2-iodo-3-nitrobenzene, finally, the nitro group is reduced to obtain 3-chloro-2-iodoaniline. |
| preparation | step a. preparation of 2-chloro -6-nitroaniline 1-chloro -3-nitrobenzene (3.1g,0.0197mol) and o-methoxyamine hydrochloride (2.02g,0.0236mol) are dissolved in N,N-dimethylformamide (15mL). The solution was added dropwise over 15 min to a suspension of cuprous chloride and potassium tert-butoxide (11.07g,0.965 mol) in N,N-dimethylformamide (15 mL) cooled in a bath at 15°C. Remove the cold bath; bring the mixture to room temperature and stir for 1 hour. The reaction was quenched with aqueous ammonium chloride solution and extracted with ethyl acetate (4 × 100mL). The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried with sodium sulfate, concentrated under vacuum, and purified by silica gel column chromatography to give the title compound 2-chloro-6-nitroaniline. Step B. Preparation of 1-chloro-2-iodo-3-nitrobenzene 2-chloro-6-nitroaniline (1.0g,0.0058mol) was dissolved in hydrochloric acid (10mL) and cooled in an ice bath. Then a solution of sodium nitrite (0.68g,0.0098mol) in water (10mL) was added very slowly under stirring. After 15 minutes, the reaction mixture was filtered through glass wool to a solution of potassium iodide (4.1g,0.024mol) in water (10mL). Stir the resulting orange mixture overnight at room temperature. It was then extracted with ethyl acetate and washed with 10% aqueous sodium hydroxide solution (50mL). The organic layer was washed with a saturated sodium chloride aqueous solution and concentrated in vacuum to obtain the title compound 1-chloro-2-iodo-3-nitrobenzene. Step C. Preparation of 3-chloro-2-iodoaniline Stannous chloride dihydrate (5.5g,0.0245tool) is added in batches to a solution of stirred 1-chloro-2-iodo-3-nitrobenzene (1.4g,0.00490 mol) in ethanol (20 mL) at 0°C. The reaction mixture was stirred at 70°C for 30 minutes. The reaction mixture was concentrated and diluted with ice-cold water (150mL), and the pH was slightly alkaline by the addition of an aqueous solution of saturated sodium carbonate, followed by extraction with ethyl acetate (4 × 100mL). The combined organic layer is washed with a saturated sodium chloride aqueous solution, dried with sodium sulfate and concentrated in vacuum to obtain the title compound 3-chloro-2-iodoaniline |
Last Update：2024-04-10 22:29:15
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