Bromonitromethane
- CAS NO.:563-70-2
- Empirical Formula: CH2BrNO2
- Molecular Weight: 139.94
- MDL number: MFCD00007401
- EINECS: 209-258-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-15 10:43:51
What is Bromonitromethane?
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.
The Uses of Bromonitromethane
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.
The Uses of Bromonitromethane
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
What are the applications of Application
Bromonitromethane is used in production of various protected α-bromo nitroalkane donors
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.
Properties of Bromonitromethane
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 |
form | Liquid |
pka | 7.22±0.29(Predicted) |
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 for Bromonitromethane
Signal word | Danger |
Pictogram(s) |
Flame Over Circle Oxidizers GHS03 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H272:Oxidising liquids;Oxidising solids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Bromonitromethane
New Products
6-Bromo 2-Iodo Indole Pyridine 2,4,6-Tricarboxaldehyde Fosfomycin EP impurity D Rimegepant Impurity 3 Ivermectin EP Impurity B Tubulysin I (R)-tert-butyl (4-methyl-1-oxopentan-3-yl)carbamate Tubulysin F Tubulysin E Calcium Sodium Phosphosilicate IH Imeglimin Hydrochloride IH (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 2-(1-(Mercaptomethyl) cyclopropyl) acetonitrile 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate 1-(4-Fluorophenyl)piperidin-2-one Benzene butanoic acid, 2-hydroxy-3-iodo-, methyl ester 3-Morpholino-5,6-dihydropyridin-2(1H)-one 4-Bromo-N,N-bis(4-iodophenyl)aniline 2-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 3,6-Bis(4-iodophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 3-bromo-5-fluorobenzaldehyde 2-chloro-(4-Trifluoromethyl) benzyl bromide 3-Fluro-6,7-dihydro-5H-Pyrrolo [3,4-b]pyridine dihydro chlorideRelated products of tetrahydrofuran
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