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731536

Sigma-Aldrich

3-Oxetanone

Synonym(s):

1,3-Epoxy-2-propanone

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About This Item

Empirical Formula (Hill Notation):
C3H4O2
CAS Number:
6704-31-0
Molecular Weight:
72.06
MDL number:
MFCD09263255
UNSPSC Code:
12352100
PubChem Substance ID:
329764664
NACRES:
NA.22

form

liquid

Quality Level

100

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

Related Categories

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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

79.0 °F - closed cup

Flash Point(C)

26.1 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5676
MKCP7087
MKCM5966
MKCK4893
MKCH8402

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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.
Oxetanes as promising modules in drug discovery
Wuitschik G, et al.
Angewandte Chemie (International Edition in English), 45(46), 7736-7739 (2006)
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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