Chemistry:3,3-Bis(chloromethyl)oxetane

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3,3-Bis(chloromethyl)oxetane
Bis(chloromethyl)oxetane.svg
3,3-Bis(chloromethyl)oxetane-3D-balls-by-AHRLS-2012.png
3,3-Bis(chloromethyl)oxetane-3D-sticks-by-AHRLS-2012.png
3,3-Bis(chloromethyl)oxetane-3D-vdW-by-AHRLS-2012.png
Names
Preferred IUPAC name
3,3-Bis(chloromethyl)oxetane
Other names
3,3-Dichloromethyloxycyclobutane
BCMO
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 201-136-5
UNII
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 pictograms GHS07: Harmful GHS06: Toxic
GHS Signal word Warning
H302, H330, H315, H319, H335
P260, P264, P270, P271, P280, P284, P301+312, P302+352, P304+340, P305+351+338, P310, P320, P321, P330, P332+313, P337+313, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

3,3-Bis(chloromethyl)oxetane (BCMO) is an intermediate in the synthesis of poly(bis(azidomethyl)oxetane (PolyBAMO), an energetic polymer that is being studied for use as a propellant binder for rocket fuel.[2]

It is classified as an extremely hazardous substance in the United States .[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. ↑ 1.0 1.1 1.2 Oxetane, 3,3-bis(chloromethyl)- at hazmap.nlm.nih.gov.
  2. ↑ [2]http://www.dtic.mil/dtic/tr/fulltext/u2/a377866.pdf
  3. ↑ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities". Government Printing Office. http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf. 
  4. ↑ 4.0 4.1 Pisharath, Sreekumar; Ang, How Ghee (2007). "Synthesis and thermal decomposition of GAP–Poly(BAMO) copolymer" (in en). Polymer Degradation and Stability 92 (7): 1365–1377. doi:10.1016/j.polymdegradstab.2007.03.016. 



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