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| | Bromonitromethane Basic information |
| | Bromonitromethane Chemical Properties |
| Melting point | -28 °C | | Boiling point | 146-148 °C/750 mmHg (lit.) | | density | 2.007 g/mL at 25 °C (lit.) | | refractive index | 1.485-1.495 | | Fp | 4°C | | solubility | Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slig | | pka | 7.22±0.29(Predicted) | | form | Liquid | | color | Clear yellow | | Stability: | Light Sensitive, Volatile | | CAS DataBase Reference | 563-70-2(CAS DataBase Reference) | | EPA Substance Registry System | Methane, bromonitro- (563-70-2) |
| | Bromonitromethane Usage And Synthesis |
| Chemical Properties | Bromonitromethane is a clear yellow liquid, It is a strong oxidizing agent with properties similar to nitromethane.
Bromonitromethane has been used:
in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesis.
in preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reaction.
in diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy.
| | Uses | Bromonitromethane has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates.
Bromonitromethane is a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the interesting 3-azabicyclo[ 3.1.0]hexane ring system.
it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzothio-phenes, and nitrothiazoles, polyfunctionalized nitrocyclopropanes. It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes. In addition, it could be used as a bromine donor. | | Uses | Bromonitromethane has been used:
- in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesis
- in preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reaction
- in diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy
| | Preparation | Bromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. A typical procedure is as following: freshly distilled nitromethane was stirred at 0℃ and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification.
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| | Bromonitromethane Preparation Products And Raw materials |
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