3,3-Bis(azidomethyl)oxetane

3,3-Bis(azidomethyl)oxetane
Names
	IUPAC name 3,3-bis(azidomethyl)oxetane
Identifiers
CAS Number	59595-53-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	BAMO
PubChem CID	12725338;
CompTox Dashboard (EPA)	DTXSID40508156 ;
	InChI 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

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]

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]

References

^ ^a ^b ^c Pisharath, Sreekumar; Ang, How Ghee (2007). "Synthesis and thermal decomposition of GAP–Poly(BAMO) copolymer". Polymer Degradation and Stability. 92 (7): 1365–1377. doi:10.1016/j.polymdegradstab.2007.03.016.
^ Lee, Young Joo; Tang, Ching-Jen; Kudva, Gautam; Litzinger, Thomas A. (1998). "Thermal Decomposition of 3,3'-Bis-Azidomethyl-Oxetane". Journal of Propulsion and Power. 14 (1): 37–44. doi:10.2514/2.5263. ISSN 0748-4658.
^ Zhang, Chi; Li, Jie; Luo, Yunjun; Yan, Shi (2016-01-02). "Synthesis and thermal decomposition of 3,3'-bis-azidomethyl oxetane-3-azidomethyl-3'-methyl oxetane random copolymer". Soft Materials. 14 (1): 9–14. doi:10.1080/1539445X.2015.1089904. ISSN 1539-445X. S2CID 100659161.
^ Nair, J. K.; Satpute, R. S.; Polke, B. G.; Mukundan, T.; Asthana, S. N.; Singh, Haridwar (2002-04-01). "Synthesis and Characterisation of Bis-azido Methyl Oxetane and its Polymer and Copolymer with Tetrahydrofuran". Defence Science Journal. 52 (2): 147–156. doi:10.14429/dsj.52.2159. S2CID 98035395. Archived from the original on 2020-09-28. Retrieved 2022-03-21.

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[:0-1] Pisharath, Sreekumar; Ang, How Ghee (2007). "Synthesis and thermal decomposition of GAP–Poly(BAMO) copolymer". Polymer Degradation and Stability. 92 (7): 1365–1377. doi:10.1016/j.polymdegradstab.2007.03.016.

[2] Lee, Young Joo; Tang, Ching-Jen; Kudva, Gautam; Litzinger, Thomas A. (1998). "Thermal Decomposition of 3,3'-Bis-Azidomethyl-Oxetane". Journal of Propulsion and Power. 14 (1): 37–44. doi:10.2514/2.5263. ISSN 0748-4658.

[3] Zhang, Chi; Li, Jie; Luo, Yunjun; Yan, Shi (2016-01-02). "Synthesis and thermal decomposition of 3,3'-bis-azidomethyl oxetane-3-azidomethyl-3'-methyl oxetane random copolymer". Soft Materials. 14 (1): 9–14. doi:10.1080/1539445X.2015.1089904. ISSN 1539-445X. S2CID 100659161.

[4] Nair, J. K.; Satpute, R. S.; Polke, B. G.; Mukundan, T.; Asthana, S. N.; Singh, Haridwar (2002-04-01). "Synthesis and Characterisation of Bis-azido Methyl Oxetane and its Polymer and Copolymer with Tetrahydrofuran". Defence Science Journal. 52 (2): 147–156. doi:10.14429/dsj.52.2159. S2CID 98035395. Archived from the original on 2020-09-28. Retrieved 2022-03-21.

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