Bromochloromethane

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Bromochloromethane
Names
IUPAC name
Bromochloromethane
Other names
Monochloromonobromomethane, Bromo(chloro)methane, Chloromethyl bromide, Methylene chlorobromide, Methylene bromochloride, Borothene, Halon 1011, BCM, CBM, UN 1887
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.752 Edit this at Wikidata
EC Number
  • 200-826-3
KEGG
RTECS number
  • PA5250000
  • InChI=1/CH2BrCl/c2-1-3/h1H2
    Key: JPOXNPPZZKNXOV-UHFFFAOYAI
  • BrCCl
Properties
CH2BrCl
Molar mass 129.38 g/mol
Appearance Colorless to yellow liquid with chloroform-like odor
Density 1.9344 g/cm3 at 20 °C
Melting point -86.5 °C
Boiling point 68.1 °C
16.7 g/l
Vapor pressure 15.6 kPa at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

It was invented for use in fire extinguishers by the Germans during the mid-40s, in an attempt to create a less-toxic, more effective alternative to carbon tetrachloride. This was a concern in aircraft and tanks as carbon tetrachloride produced highly toxic by-products when discharged onto a fire. CBM was slightly less toxic, and used up until the late 1960s, being officially banned by the NFPA for use in fire extinguishers in 1969, as safer and more effective agents such as halon 1211 and 1301 were developed. Due to its ozone depletion potential its production was banned from 1 January 2002 at the Eleventh Meeting of the Parties for the Montreal Protocol on Substances that Deplete the Ozone Layer.

A 1950s US CBM fire extinguisher.

It can be biologically decomposed using hydrolase enzyme alkylhalidase by the reaction:

CH2BrCl (l) + H2O (l) → CH2O (l) + Br2 (l) + Cl2 (g)

In fiction

In the Enter the Matrix video game, the player can find a "Chloro-Bromo Methane Gun", which is used as a fire extinguisher. It fires a pressurized cartridge of CBM gas to put out fires. However, due to its chemical properties, firing a cartridge near people causes their lungs to fill with liquid, effectively drowning them.

External links

  • International Chemical Safety Card 0392
  • NIOSH Pocket Guide to Chemical Hazards. "#0123". National Institute for Occupational Safety and Health (NIOSH).
  • MSDS at Oxford University
  • MSDS at Oxford University (deuterated bromochloromethane)
  • Notice with Respect to n-Propyl Bromide and Bromochloromethane
  • Chemical fact sheet
  • Data sheet at arbemarle.com