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3,3-Bis(azidomethyl)oxetane

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3,3-Bis(azidomethyl)oxetane
Names
IUPAC name 3,3-bis(azidomethyl)oxetane
Identifiers
CAS Number
3D model (JSmol)
Abbreviations BAMO
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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==)CN==
Properties
Chemical formula C5H8N6O
Molar mass 168.160 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.

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.

References

  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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