3,3-Bis(chloromethyl)oxetane

3,3-Bis(chloromethyl)oxetane (BCMO) is an intermediate in the synthesis of poly(bis(azidomethyl)oxetane (PolyBAMO), an energetic polymer that is being studied for use as a propellant binder for rocket fuel.

It is classified as an extremely hazardous substance in the United States. It can cause kidney damage, lacrimation, and somnolence if consumed.

Preparation and reaction
BCMO is formed in solution via cyclization of pentaerythritol trichlorohydrin with a non-organic base like sodium hydroxide.

BAMO can be formed from a reaction of BCMO with sodium azide. This reaction takes place in an alkaline solution with tetrabutyl ammonium bromide, which acts as a phrase transfer catalyst.