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Oxetane information


Oxetane
Names
Preferred IUPAC name
Oxetane[1]
Systematic IUPAC name
1,3-Epoxypropane
Oxacyclobutane
Other names
1,3-Propylene oxide
Trimethylene oxide
Identifiers
CAS Number
  • 503-30-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
102382
ChEBI
  • CHEBI:30965 checkY
ChemSpider
  • 9994 checkY
ECHA InfoCard 100.007.241 Edit this at Wikidata
EC Number
  • 207-964-3
Gmelin Reference
239520
PubChem CID
  • 10423
UNII
  • I279Q16FU6 checkY
UN number 1280
CompTox Dashboard (EPA)
  • DTXSID8025969 Edit this at Wikidata
InChI
  • InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2 checkY
    Key: AHHWIHXENZJRFG-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O/c1-2-4-3-1/h1-3H2
    Key: AHHWIHXENZJRFG-UHFFFAOYAE
SMILES
  • C1CCO1
Properties
Chemical formula
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)
1.3895 at 25 °C
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H225, H302, H312, H332
Precautionary statements
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

The term "an oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring.

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 147. doi:10.1039/9781849733069-FP001 (inactive 2024-04-15). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)

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Oxetane

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atoms and one oxygen atom. The term "an oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring. A typical well-known method of...

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Polyoxetane

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or poly(oxetane), is synthetic organic heteroatomic thermoplastic polymer with molecular formula (–OCH2CH2CH2–)n. It is polymerized from oxetane monomer...

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Tetrahydrofuran

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2-Methyltetrahydrofuran Trapp mixture Other cyclic ethers: oxirane (C 2H 4O), oxetane (C 3H 6O), oxane (C 5H 10O) "New IUPAC Organic Nomenclature - Chemical...

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Trimethylolpropane

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are precursors to high-gloss coatings and ion exchange resins. The oxetane "TMPO" is a photoinduceable polymerisation initiator. It is may also be...

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Chemical reaction

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In this Paterno–Büchi reaction, a photoexcited carbonyl group is added to an unexcited olefin, yielding an oxetane....

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Propylene oxide

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to distinguish it from its isomer 1,3-propylene oxide, better known as oxetane. Industrial production of propylene oxide starts from propylene. Two general...

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Heterocyclic compound

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Heteroatom Saturated Unsaturated Nitrogen Azetidine Azete Oxygen Oxetane Oxete Phosphorus Phosphetane Phosphete Sulfur Thietane Thiete...

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C3H6O

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methyl vinyl ether or methoxyethene, H3C-O-CH=CH2, CAS number: 107-25-5 oxetane or trimethylene oxide, cyclo(-CH2-CH2-O-CH2-), CAS number: 503-30-0 1,2-epoxy-propane...

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Malonic anhydride

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Malonic anhydride or oxetane-2,4-dione is an organic compound with chemical formula C3H2O3 or CH2(CO)2O. It can be viewed as the anhydride of malonic...

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Structural isomer

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trans stereoisomeric forms Acetone –94.9 56.53 Tautomeric with propen-2-ol Oxetane –97 48 Propylene oxide –112 34 Has two enantiomeric forms Methyl vinyl...

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Jacobsen epoxidation

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complex. There are three major pathways. The concerted pathway, the metalla oxetane pathway and the radical pathway. The most accepted mechanism is the concerted...

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Cationic polymerization

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Cationic ring-opening polymerization of oxetane involving (a and b) initiation, (c) propagation, and (d) termination with methanol...

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EPA list of extremely hazardous substances

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N-Nitrosodimethylamine Norbormide Organorhodium complex Ouabain Oxamyl Oxetane, 3,3-bis(chloromethyl)- Oxydisulfoton Paraquat Paraquat methosulfate Parathion...

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Nicolaou Taxol total synthesis

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(ring B). The third pre-assembled part is an amide tail. Ring D is an oxetane ring fused to ring C. Two key chemical transformations are the Shapiro...

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Enolate

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are shown below: Alkylation of aza enolates via epoxide ring opening of oxetane Since epoxide is a three-membered ring molecule, it has a high degree of...

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Polytetrahydrofuran

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Dreyfuss, P.; Dreyfuss, M. P. (1996). "Polyethers, Tetrahydrofuran and Oxetane Polymers". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley...

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Diketene

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formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorless...

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Oxetene

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heterocycle. The compound is unstable and has been synthesized. Compared to oxetane, the saturated compound, oxetene is destabilized because the double bond...

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C3H2O3

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organic compound; the anhydride of malonic acid, or a double ketone of oxetane Vinylene carbonate, simplest unsaturated cyclic carbonic acid ester This...

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Azetidine

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P363, P370+P378, P403+P235, P405, P501 Related compounds Other anions Oxetane, Phosphetane, Thietane Related compounds Aziridine, Diazetidine, Pyrrolidine...

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Paclitaxel total synthesis

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cyclohexene), ring B (a cyclooctane), ring C (a cyclohexane) and ring D (an oxetane). The paclitaxel drug development process took over 40 years. The anti-tumor...

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Alkyl ketene dimer

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central structural element of propiolactone and diketene. Attached to the oxetane ring of technically relevant alkyl ketene dimers there is a C12 – C16 alkyl...

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Paclitaxel

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the pathway, an oxidation at C9 forms a ketone functional group and an oxetane, forming the intermediate baccatin III. The final steps of the pathway...

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