Bromofluoromethane

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Bromofluoromethane
Bromofluoromethane.png
Bromofluoromethane-3D-vdW.png
Identifiers
CAS number 373-52-4
PubChem 61108
ChemSpider 55059 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula CH2BrF
Molar mass 112.93 g/mol
Appearance Gas
Boiling point 19 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Bromofluoromethane is a mixed gaseous halomethane soluble in alcohol and very soluble in chloroform.

Its standard molar entropy, Sogas is 276.3 J/(mol K) and heat capacity, cp is 49.2 J/(mol K).

Preparation[edit]

Up to date, it has been prepared by three prevailingly ineffective methods:

  1. From salts of fluoroacetic acid using a Hunsdiecker type of reaction.
  2. From dibromofluoromethane by reductive debromination with a Swarts reagent.
  3. From a dihalomethane by an halogen exchange reaction or from a halomethane by catalyzed bromination or fluorination.

The method with the highest yield is reductive debromination of dibromofluoromethane using an organotin hydride.[1]

Uses[edit]

Bromofluoromethane is an important reagent in the manufacture of intermediates, pharmaceuticals and other chemicals. Usage of bromofluoromethane is regulated due to its ozone depletion potential (0.73). Its isotopomer CH2Br18F is used in radiochemistry.

References[edit]

  1. ^ Debrominating dibromofluoromethane with tributyltin hydride
  • G. Cazzoli, C. Puzzarini, A. Baldacci and A. Baldan (2007). "Determination of the molecular dipole moment of bromofluoromethane: microwave Stark spectra and ab initio calculations". J. Mol. Spectrosc. 241 (115). doi:10.1016/j.jms.2006.11.004. 

External sources[edit]