731536
3-Oxetanone
Sinónimos:
1,3-Epoxy-2-propanone
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About This Item
Fórmula empírica (notación de Hill):
C3H4O2
Número de CAS:
Peso molecular:
72.06
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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form
liquid
Quality Level
availability
not available in EU
refractive index
n20/D 1.426
density
1.124 g/mL at 25 °C
functional group
ether
ketone
storage temp.
−20°C
SMILES string
O=C1COC1
InChI
1S/C3H4O2/c4-3-1-5-2-3/h1-2H2
InChI key
ROADCYAOHVSOLQ-UHFFFAOYSA-N
General description
Product may polymerize over time during storage.
Application
3-Oxetanone can be used to synthesize:
- Various oxetane-containing lead compounds with improved solubility, reduced lipophilicity and amphiphilicity.
- (Hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles via single-step microwave mediated reaction with primary amides and thioamides, respectively.
- Oxetane containing spirocycles through thermal 1,3-dipolar cycloaddition reaction with α-amino acids or secondary α-amino acid esters.
signalword
Danger
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
79.0 °F - closed cup
flash_point_c
26.1 °C - closed cup
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Angewandte Chemie (International Edition in English), 45(46), 7736-7739 (2006)
Emily M Wright et al.
The journal of physical chemistry. A, 119(29), 7966-7972 (2015-06-25)
The pyrolysis products of gas-phase 3-oxetanone were identified via matrix-isolation Fourier transform infrared spectroscopy and photoionization mass spectrometry. Pyrolysis was conducted in a hyperthermal nozzle at temperatures from 100 to 1200 °C with the dissociation onset observed at ∼600 °C.
Single-Step Microwave-Mediated Synthesis of Oxazoles and Thiazoles from 3-Oxetanone: A Synthetic and Computational Study
Orr D, et al.
Chemistry?A European Journal , 19(29), 9655-9662 (2013)
Synthesis of oxetane/azetidine containing spirocycles via the 1, 3-dipolar cycloaddition reaction
Jones B, et al.
Tetrahedron Letters, 57(25), 2811-2813 (2016)
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