3,3-Bis(azidomethyl)oxetane

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3,3-Bis(azidomethyl)oxetane
3,3-Bis(azidomethyl)oxetane.svg
Names
IUPAC name
3,3-bis(azidomethyl)oxetane
Identifiers
3D model (JSmol)
AbbreviationsBAMO
ChemSpider
PubChem CID
  • Key: GOPVUFFWLXPUBM-UHFFFAOYSA-N
  • InChI=1S/C5H8N6O/c6-10-8-1-5(2-9-11-7)3-12-4-5/h1-4H2
  • C1C(CO1)(CN=[N+]=[N-])CN=[N+]=[N-]
Properties
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).

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

  1. 1 2 3 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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