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Bromonitromethane

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Bromonitromethane Basic information

Product Name:
Bromonitromethane
Synonyms:
  • BROMONITROMETHANE
  • Bromonitromethane, tech.
  • bromonitro-methan
  • Methane, bromonitro-
  • nitrobromomethane
  • bromonitromethane CH2BrNO2
  • Bromonitromethane, 90%,tech.
  • Nitromethyl bromide
CAS:
563-70-2
MF:
CH2BrNO2
MW:
139.94
EINECS:
209-258-0
Product Categories:
  • PHARMACEUTICAL INTERMEDIATES
  • Nitro Compounds
  • Nitrogen Compounds
  • Organic Building Blocks
Mol File:
563-70-2.mol
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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
Flash point:
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)
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Safety Information

Hazard Codes 
Xn-O,Xi,O
Risk Statements 
8-36/37/38-20/21/22
Safety Statements 
36/37/39-26-17-36
RIDADR 
3098
WGK Germany 
3
RTECS 
PA5360000
HazardClass 
5.1
PackingGroup 
III
HS Code 
29049095

MSDS

  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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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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