Are there any molecules that are chiral that are also gases at room temperature?
Failing that, what chiral molecules have a high vapor pressure? Propylene oxide has a boiling point of only 34 C, so that seems like a good one. Are there others?
EDIT: I appreciate all of the great suggestions! I should have mentioned before, but I am looking for something that can be purchased in both R and S enantiomers.
The molecule has to be small. trans-1,2-difluorocyclopropane is certainly chiral, and its predicted boiling point is ~ 5 deg C. trans-1,1,2,3-tetrafluorocyclopropane is another likely candidate. This one will be easier to prepare (from perfluoropropylene oxide and trans-1,2-difluoroethylene).
Separation of enantiomers is the hard part.
1-Chloro-1,2,2,2-tetrafluoroethane has bp -12 Celsium. For comparison, 1-chloro-1-fluoroethane has bp +16 Celsium. In most cases, replacing good share of hydrogen in an organic molecule with fluorine leads to significant decrease of bp. perfluoropropylene oxide has bp -27 Celsium, comparing to +34 of vanilla propylene oxide you noted.
Considering molecules that have been prepared and resolved:
1,3-dimethylallene (2,3-pentadiene) boils a bit above room temperature at 48.5 C (see page 11 of this reference for the experimental preparation), but likely has a reasonable vapor pressure since it has a lower molecular weight than pentane. The advantage to this molecule is that it has already been (at least) partially resolved (see here and here) in a one-step hydroboration.
Another simple hydrocarbon to consider is trans-cyclooctene. It has a higher boiling point (143 C) but a significant vapor pressure, it flashes at 25 C. The molecule is chiral and has also been resolved.
If you use deuterium and tritium, you can make stereocenters from methyl groups. For example, 1-deutero-1-tritioethane is be chiral.
