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3,3-Bis(chloromethyl)oxetane

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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 phase transfer catalyst.[4]

References

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