3,3-Bis(chloromethyl)oxetane

3,3-Bis(chloromethyl)oxetane
Names
	Preferred IUPAC name 3,3-Bis(chloromethyl)oxetane
	Other names 3,3-Dichloromethyloxycyclobutane; BCMO
Identifiers
CAS Number	78-71-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	6302;
ECHA InfoCard	100.001.033
EC Number	201-136-5;
PubChem CID	6550;
UNII	N12TP81ATK ;
CompTox Dashboard (EPA)	DTXSID9058816 ;
	InChI 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;
	SMILES ClCC1(CCl)COC1;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H330, H335
Precautionary statements	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)	3 1 0
	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(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

Oxetane, 3,3-bis(chloromethyl)- at hazmap.nlm.nih.gov.
[2]http://www.dtic.mil/dtic/tr/fulltext/u2/a377866.pdf Archived 2018-08-20 at the Wayback Machine
"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.
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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[hazmap-1] 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

[gov-right-know-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.

[:0-4] 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.