Bromonitromethane
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
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)
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
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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