Bromofluoromethane

Bromofluoromethane
Names
Preferred IUPAC name
Bromo(fluoro)methane
Other names
Bromofluoromethane
Bromofluoromethylene
CFC 31B1
R 31B1
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.117.922 Edit this at Wikidata
UNII
  • InChI=1S/CH2BrF/c2-1-3/h1H2 checkY
    Key: LHMHCLYDBQOYTO-UHFFFAOYSA-N checkY
  • InChI=1/CH2BrF/c2-1-3/h1H2
  • C(F)Br
  • BrCF
Properties
CH2BrF
Molar mass 112.93 g/mol
Appearance Gas
Boiling point 19 °C (66 °F; 292 K)
Structure
Tetrahedral
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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

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 contains fluorine-18 (18F) and is used in radiochemistry.

References

  1. ^ Debrominating dibromofluoromethane with tributyltin hydride
  • G. Cazzoli; C. Puzzarini; A. Baldacci & A. Baldan (2007). "Determination of the molecular dipole moment of bromofluoromethane: microwave Stark spectra and ab initio calculations". J. Mol. Spectrosc. 241 (115): 112–115. Bibcode:2007JMoSp.241..112C. doi:10.1016/j.jms.2006.11.004.

External sources