4-Iodo-2-nitroanisole

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4-Iodo-2-nitroanisole Basic information
Product Name:4-Iodo-2-nitroanisole
Synonyms:4-IODO-2-NITROANISOLE;4-iodo-1-methoxy-2-nitrobenzene;Benzene, 4-iodo-1-methoxy-2-nitro-
CAS:52692-09-8
MF:C7H6INO3
MW:279.03
EINECS:
Product Categories:
Mol File:52692-09-8.mol
4-Iodo-2-nitroanisole Structure
4-Iodo-2-nitroanisole Chemical Properties
Melting point 96-98°C
Boiling point 330.8±27.0 °C(Predicted)
density 1.893±0.06 g/cm3(Predicted)
storage temp. 2-8°C, protect from light
AppearanceLight yellow to yellow Solid
Sensitive Light Sensitive
Safety Information
Risk Statements 23/24/25
Safety Statements 36/37-45
HS Code 2909309090
MSDS Information
ProviderLanguage
ALFA English
4-Iodo-2-nitroanisole Usage And Synthesis
Synthesis Reference(s)Tetrahedron Letters, 10, p. 2427, 1969 DOI: 10.1017/S0009838800024678
Synthesis
2-Nitroanisole

91-23-6

4-Iodo-2-nitroanisole

52692-09-8

General procedure for the synthesis of 4-iodo-2-nitroanisole from 2-nitroanisole: To a stirred solution of 2-nitroanisole (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was added sequentially Ph3PAuNTf2 (0.025 mmol, 19 mg; if using the 2:1 complex of Ph3PAuNTf2 with toluene) and N-iodosuccinimide (NIS, 1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of the feedstock was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents, resulting in pure 4-iodo-2-nitroanisole.

References[1] Synlett, 2014, vol. 25, # 3, p. 399 - 402
[2] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3552 - 3555
[3] Tetrahedron, 2004, vol. 60, # 41, p. 9113 - 9119
[4] Synthetic Communications, 2007, vol. 37, # 8, p. 1259 - 1265
[5] Synthesis, 2006, # 7, p. 1195 - 1199
4-Iodo-2-nitroanisole Preparation Products And Raw materials
Raw materials2-Nitroanisole-->4-Iodoanisole-->3-Methoxy-2-nitrobenzoic acid-->1,2-Dichloroethane-->N-Iodosuccinimide-->Toluene-->Triphenylphosphine-->GOLD
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