3,3-Bis(chloromethyl)oxetane

Last updated
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
ECHA InfoCard 100.001.033 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-136-5
PubChem CID
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
AppearanceBlack 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:
GHS-pictogram-exclam.svg GHS-pictogram-skull.svg
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)
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]

Related Research Articles

<span class="mw-page-title-main">Nickel tetracarbonyl</span> Chemical compound

Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a nickel(0) organometallic compound with the formula Ni(CO)4. This colorless liquid is the principal carbonyl of nickel. It is an intermediate in the Mond process for producing very high-purity nickel and a reagent in organometallic chemistry, although the Mond Process has fallen out of common usage due to the health hazards in working with the compound. Nickel carbonyl is one of the most dangerous substances yet encountered in nickel chemistry due to its very high toxicity, compounded with high volatility and rapid skin absorption.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Chloroacetic acid</span> Chemical compound

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

<span class="mw-page-title-main">Polyglycolide</span> Chemical compound

Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization. PGA has been known since 1954 as a tough fiber-forming polymer. Owing to its hydrolytic instability, however, its use has initially been limited. Currently polyglycolide and its copolymers (poly(lactic-co-glycolic acid) with lactic acid, poly(glycolide-co-caprolactone) with ε-caprolactone and poly (glycolide-co-trimethylene carbonate) with trimethylene carbonate) are widely used as a material for the synthesis of absorbable sutures and are being evaluated in the biomedical field.

Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula C
3
H
6
O
, having a four-membered ring with three carbon atoms and one oxygen atom.

<span class="mw-page-title-main">Vinyl acetate</span> Chemical compound

Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers.

<span class="mw-page-title-main">Cycloheximide</span> Chemical compound

Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus. Cycloheximide exerts its effects by interfering with the translocation step in protein synthesis, thus blocking eukaryotic translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro. It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium.

<span class="mw-page-title-main">Adiponitrile</span> Chemical compound

Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.

Polysulfones are a family of high performance thermoplastics. These polymers are known for their toughness and stability at high temperatures. Technically used polysulfones contain an aryl-SO2-aryl subunit. Due to the high cost of raw materials and processing, polysulfones are used in specialty applications and often are a superior replacement for polycarbonates.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

<span class="mw-page-title-main">Superabsorbent polymer</span> Polymers that can absorb and retain extremely large amounts of a liquid relative to their own mass

A superabsorbent polymer (SAP) (also called slush powder) is a water-absorbing hydrophilic homopolymers or copolymers that can absorb and retain extremely large amounts of a liquid relative to its own mass.

<span class="mw-page-title-main">Chloromethyl methyl ether</span> Chemical compound

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group, and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.

<span class="mw-page-title-main">Bis(chloromethyl) ether</span> Chemical compound

Bis(chloromethyl) ether is an organic compound with the chemical formula (CH2Cl)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale, but was found to be highly carcinogenic and thus such production has ceased.

<span class="mw-page-title-main">Cyanuric fluoride</span> Chemical compound

Cyanuric fluoride or 2,4,6-trifluoro-1,3,5-triazine is a chemical compound with the formula (CNF)3. It is a colourless, pungent liquid. It has been used as a precursor for fibre-reactive dyes, as a specific reagent for tyrosine residues in enzymes, and as a fluorinating agent.

<span class="mw-page-title-main">Carbophenothion</span> Chemical compound

Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.

<span class="mw-page-title-main">Bis(chloromethyl) ketone</span> Chemical compound

Bis(chloromethyl) ketone is a chemical substance with formula C
3
H
4
Cl
2
O
. It is a solid, and is used in the making of citric acid. Exposures such as contact or inhalation of bis(chloromethyl) ketone can result in irritation or damage to skin, eyes, throat, lungs, liver and kidneys, as well as headaches and fainting.

<span class="mw-page-title-main">3,4-Dichlorophenyl isocyanate</span> Chemical compound

3,4-Dichlorophenyl isocyanate is a chemical compound used as a chemical intermediate and in organic synthesis. It is a solid, and ranges in colour from white to yellow. It is an irritant for tissues including eyes and mucous membranes, and inhalation of dust from the chemical is poisonous. It can be used industrially in the preparation of triclocarban by reaction with p-chloroaniline.

<span class="mw-page-title-main">3,3-Bis(azidomethyl)oxetane</span> Chemical compound

3,3-Bis(azidomethyl)oxetane (BAMO) is a oxetane monomer used in energetic propellant binders and plasticizer. It is frequently used as a copolymer to improve the physical properties of more commonly used polymers and to give them energetic properties.

Polyoxetane (POX), or poly(oxetane), is synthetic organic heteroatomic thermoplastic polymer with molecular formula (–OCH2CH2CH2–)n. It is polymerized from oxetane monomer, which is a four-membered cyclic ether.

References

  1. 1 2 3 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. 1 2 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.