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563-70-2
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???(??):
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Bromonitromethane
???(??):
255858_ALDRICH;EINECS 209-258-0;bromonitro-methan;nitrobromomethane;BROMONITROMETHANE;Nitromethyl bromide;Methane, bromonitro-;Bromonitromethane, tech.;bromonitromethane CH2BrNO2;Bromonitromethane, 90%,tech.
CBNumber:
CB7381067
???:
CH2BrNO2
??? ??:
139.94
MOL ??:
563-70-2.mol
MSDS ??:
SDS

?????????? ??

???
-28 °C
?? ?
146-148 °C/750 mmHg (lit.)
??
2.007 g/mL at 25 °C (lit.)
???
1.485-1.495
???
4°C
???
Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slig
?? ?? (pKa)
7.22±0.29(Predicted)
??? ??
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CAS ??????
563-70-2(CAS DataBase Reference)
EPA
Methane, bromonitro- (563-70-2)
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  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xn-O,Xi,O
?? ???? ?? 8-36/37/38-20/21/22
????? 36/37/39-26-17-36
????(UN No.) 3098
WGK ?? 3
RTECS ?? PA5360000
?? ?? 5.1
???? III
HS ?? 29049095
???? ?? KE-03689
????(GHS): GHS hazard pictogramsGHS hazard pictograms
?? ?: Danger
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H272 ??? ???? ?; ??? ??? ??;??? ?? ?? 2
?? 3
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GHS hazard pictograms P210, P220, P221P280, P370+P378,P501
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
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P210 ?·???·??·????? ????? - ?? ???.
P302+P352 ??? ??? ??? ?? ????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.

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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.

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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.

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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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