Chemistry:Bromofluoromethane

Bromofluoromethane

Names
Preferred IUPAC name Bromo(fluoro)methane
Other names Bromofluoromethane Bromofluoromethylene CFC 31B1 R 31B1
Identifiers
CAS Number	373-52-4 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	55059 Y
PubChem CID	61108
UNII	22205E7CEM Y
InChI InChI=1S/CH2BrF/c2-1-3/h1H2 Y Key: LHMHCLYDBQOYTO-UHFFFAOYSA-N Y 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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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.

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

• 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. doi:10.1016/j.jms.2006.11.004. Bibcode: 2007JMoSp.241..112C. 

External sources

• Determination of the molecular dipole moment of bromofluoromethane
• http://www.valliscor.com/bromofluoromethane