Bromofluoromethane

Bromofluoromethane

Names
IUPAC name Bromofluoromethane
Other names Bromofluoromethylene, CFC 31B1, R 31B1
Identifiers
CAS Number	373-52-4
ChemSpider	55059
Jmol interactive 3D	Image Image
PubChem	61108
InChI InChI=1S/CH2BrF/c2-1-3/h1H2 Key: LHMHCLYDBQOYTO-UHFFFAOYSA-N InChI=1/CH2BrF/c2-1-3/h1H2
SMILES C(F)Br BrCF
Properties
Chemical formula	CH2BrF
Molar mass	112.93 g/mol
Appearance	Gas
Boiling point	19 °C (66 °F; 292 K)
Structure
Molecular shape	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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Infobox references

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

Its standard molar entropy, S^o_gas is 276.3 J/(mol K) and heat capacity, c_p 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 is used in radiochemistry.

References

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

• Determination of the molecular dipole moment of bromofluoromethane