Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula C
3H
6O, having a four-membered ring with three carbon atoms and one oxygen atom.
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Names | |||
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Preferred IUPAC name
Oxetane[1] | |||
Systematic IUPAC name
1,3-Epoxypropane Oxacyclobutane | |||
Other names
1,3-Propylene oxide
Trimethylene oxide | |||
Identifiers | |||
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3D model (JSmol)
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102382 | |||
ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.007.241 | ||
EC Number |
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239520 | |||
PubChem CID
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UNII |
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UN number | 1280 | ||
CompTox Dashboard (EPA)
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Properties | |||
C3H6O | |||
Molar mass | 58.08 g/mol | ||
Density | 0.8930 g/cm3 | ||
Melting point | −97 °C (−143 °F; 176 K) | ||
Boiling point | 49 to 50 °C (120 to 122 °F; 322 to 323 K) | ||
Refractive index (nD)
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1.3895 at 25 °C | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H302, H312, H332 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, P501 | |||
Flash point | −28.3 °C; −19.0 °F; 244.8 K (NTP, 1992) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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The term "an oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring.
A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C:[2]
Yield of oxetane made this way is c. 40%, as the synthesis can lead to a variety of by-products including water, potassium chloride, and potassium acetate.
Another possible reaction to form an oxetane ring is the Paternò–Büchi reaction. The oxetane ring can also be formed through diol cyclization[3] as well as through decarboxylation of a six-membered cyclic carbonate.[citation needed]
More than a hundred different oxetanes have been synthesized.[4] Functional groups can be added into any desired position in the oxetane ring, including fully fluorinated (perfluorinated) and fully deuterated analogues. Major examples are:
Name | Structure | Boiling point, Bp [°C] |
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3,3-Bis(chloromethyl)oxetane | 198[5] | |
3,3-Bis(azidomethyl)oxetane | 165[6] | |
2-Methyloxetane | 60[4][failed verification] | |
3-Methyloxetane | 67[4][failed verification] | |
3-Azidooxetane | 122[7] | |
3-Nitrooxetane | 195[8] | |
3,3-Dimethyloxetane | 80[4][failed verification] | |
3,3-Dinitrooxetane | – |
Paclitaxel (Taxol) is an example of a natural product containing an oxetane ring. Taxol has become a major point of interest among researchers due to its unusual structure and success in the involvement of cancer treatment.[9] The attached oxetane ring is an important feature that is used for the binding of microtubules in structure activity; however little is known about how the reaction is catalyzed in nature, which creates a challenge for scientists trying to synthesize the product.[9]
Oxetane is used in one of the syntheses of Disparlure (Gypsy moth sexual pheromone).[10]
Oxetanes are less reactive than epoxides, and generally unreactive in basic conditions,[11] although Grignard reagents at elevated temperatures[12] and complex hydrides will cleave them.[13] However, the ring strain does make them much more reactive than larger rings,[14] and oxetanes decompose in the presence of even mildly acidic nucleophiles.[15] In non-nucleophilic acids, they mainly isomerize to allyl alcohols.[16]
Noble metals tend to catalyze isomerization to a carbonyl.[17]
In industry, the parent compound, oxetane polymerizes to polyoxetane in the presence of a dry acid catalyst,[18] although the compound was described in 1967 as "rarely polymerized commercially".[19]
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