3,3-Bis(azidomethyl)oxetane

3,3-Bis(azidomethyl)oxetane (BAMO) is a oxetane monomer used in energetic propellant binders and plasticizer.^[1][2] It is frequently used as a copolymer to improve the physical properties of more commonly used polymers and to give them energetic properties.^[3][1]

3,3-Bis(azidomethyl)oxetane

Names
IUPAC name 3,3-bis(azidomethyl)oxetane
Identifiers
CAS Number	17607-20-4 N
3D model (JSmol)	Interactive image
Abbreviations	BAMO
ChemSpider	10723826
PubChem CID	12725338
CompTox Dashboard (EPA)	DTXSID40508156
InChI Key: GOPVUFFWLXPUBM-UHFFFAOYSA-N InChI=1S/C5H8N6O/c6-10-8-1-5(2-9-11-7)3-12-4-5/h1-4H2
SMILES C1C(CO1)(CN=[N+]=[N-])CN=[N+]=[N-]
Properties
Chemical formula	C5H8N6O
Molar mass	168.160 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

BAMO is made by reacting BCMO with sodium azide in an alkaline solution. Tetrabutyl ammonium bromide is used as a phase-transfer catalyst in the reaction.^[1]

PolyBAMO can be made by mixing boron trifluoride diethyl etherate and BAMO in trimethylolpropane. The polymerization of BAMO destroys the oxetane ring, but the azide groups remain intact.^[4]