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3,3-Bis(chloromethyl)oxetane

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3,3-Bis(chloromethyl)oxetane
Names
Preferred IUPAC name
3,3-Bis(chloromethyl)oxetane
Other names
3,3-Dichloromethyloxycyclobutane
BCMO
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.033 Edit this at Wikidata
EC Number
  • 201-136-5
UNII
  • InChI=1S/C5H8Cl2O/c6-1-5(2-7)3-8-4-5/h1-4H2
    Key: CXURGFRDGROIKG-UHFFFAOYSA-N
  • InChI=1/C5H8Cl2O/c6-1-5(2-7)3-8-4-5/h1-4H2
    Key: CXURGFRDGROIKG-UHFFFAOYAZ
  • ClCC1(CCl)COC1
Properties
C5H8Cl2O
Molar mass 155.02 g·mol−1
Appearance Black or olive green solid[1]
Density 1.295 g/cm3
Melting point 18.9 °C (66.0 °F; 292.0 K)[1]
Boiling point 95 °C (203 °F; 368 K)
Hazards
GHS labelling:
GHS07: Exclamation mark GHS06: Toxic
Warning
H302, H315, H319, H330, H335
P260, P264, P270, P271, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P320, P321, P330, P332+P313, P337+P313, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,3-Bis(chloromethyl)oxetane (BCMO) is a useful monomer in the field of energetic materials for synthesis of poly(bis(azidomethyl)oxetane (PolyBAMO), which is being researched by numerous militaries around the world. Poly-BAMO is an energetic polymer that have potential to replace the current propellant binder formulations.[2]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[3] It can cause kidney damage, lacrimation, and somnolence if consumed.[1]

Preparation and reaction

BCMO is formed in solution via cyclization of pentaerythritol trichlorohydrin with a non-organic base like sodium hydroxide.[4]

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.[4]

References

  1. ^ a b c Oxetane, 3,3-bis(chloromethyl)- at hazmap.nlm.nih.gov.
  2. ^ [2]http://www.dtic.mil/dtic/tr/fulltext/u2/a377866.pdf Archived 2018-08-20 at the Wayback Machine
  3. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
  4. ^ a b 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.


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