Bromonitromethane Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H272May intensify fire; oxidizer

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Bromonitromethane Chemical Properties,Usage,Production

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.