| Identification | Back Directory | [Name]
2-IODO-4-METHOXYPHENYLAMINE | [CAS]
191348-14-8 | [Synonyms]
4-Amino-3-iodoanisole
2-iodo-4-methoxyaniline
4-Methoxy-2-iodoaniline
2-IODO-4-METHOXYPHENYLAMINE
4-AMino-3-iodoanisole[2-Iodo-4-Methoxyaniline] | [Molecular Formula]
C7H8INO | [MDL Number]
MFCD07776739 | [MOL File]
191348-14-8.mol | [Molecular Weight]
249.05 |
| Chemical Properties | Back Directory | [Appearance]
Brown liqui | [Boiling point ]
305.0±27.0 °C(Predicted) | [density ]
1.807±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
liquid | [pka]
3.14±0.10(Predicted) | [color ]
Brown to black |
| Hazard Information | Back Directory | [Chemical Properties]
Brown liqui | [Synthesis]
The general procedure for the synthesis of 2-iodo-4-methoxyaniline from tert-butyl (2-iodo-4-methoxyphenyl)carbamate was as follows: tert-butyl (2-iodo-4-methoxyphenyl)carbamate (3.5 g, 10.0 mmol) was slowly added to a solution of (2-iodo-4-methoxyphenyl)carbamate in dichloromethane (50 mL) at 0 °C with trifluoroacetic acid (8.9 mL, 120.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched with 2N sodium hydroxide solution (95 mL), followed by adjusting the pH to 8 with 2N hydrochloric acid (70 mL).The organic and aqueous layers were separated, and the aqueous layer was extracted with dichloromethane (2 x 70 mL). All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, n-hexane/ethyl acetate = 7:1) to give 2-iodo-4-methoxyaniline (2.12 g, 85% yield) as an orange oil. | [References]
[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
[2] Chemical Communications, 2001, # 24, p. 2732 - 2733
[3] Organic and Biomolecular Chemistry, 2003, vol. 1, # 1, p. 117 - 122
[4] Organometallics, 2013, vol. 32, # 2, p. 682 - 690
[5] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493 |
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