| Identification | More | [Name]
BROMONITROMETHANE | [CAS]
563-70-2 | [Synonyms]
BROMONITROMETHANE
bromonitro-methan
Methane, bromonitro-
nitrobromomethane
Bromonitromethane, tech.
Bromonitromethane, 90%,tech.
Nitromethyl bromide | [EINECS(EC#)]
209-258-0 | [Molecular Formula]
CH2BrNO2 | [MDL Number]
MFCD00007401 | [Molecular Weight]
139.94 | [MOL File]
563-70-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn-O,Xi,O | [Risk Statements ]
R8:Contact with combustible material may cause fire.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S17:Keep away from combustible material .
S36:Wear suitable protective clothing . | [RIDADR ]
3098 | [WGK Germany ]
3 | [RTECS ]
PA5360000 | [HazardClass ]
5.1 | [PackingGroup ]
III | [HS Code ]
29049095 |
| Hazard Information | Back Directory | [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 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. | [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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