oxan-4-one

• ChemBase ID: 37159
• Molecular Formular: C5H8O2
• Molecular Mass: 100.11582
• Monoisotopic Mass: 100.0524295
• SMILES: C1(=O)CCOCC1
• Canonical SMILES: O=C1CCOCC1
• InChI: InChI=1S/C5H8O2/c6-5-1-3-7-4-2-5/h1-4H2
• InChIKey: JMJRYTGVHCAYCT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxan-4-one
• IUPAC Traditional name: 4H-pyran-4-one, tetrahydro-
• Synonyms: oxan-4-one; Tetrahydro-4H-pyran-4-one; 4-Oxotetrahydropyran; Tetrahydro-4H-pyran-4-one; Tetrahydro-4H-pyran-4-one 97%; 四氢-4-吡喃-4-酮; 四氢-4H-吡喃-4-酮; 四氢吡喃酮

Database IDs

• CAS Number: 29943-42-8; 143562-54-3
• EC Number: 249-967-2
• MDL Number: MFCD00006581
• Beilstein Number: 106463
• PubChem SID: 161000466; 24888906; 24851869
• PubChem CID: 121599

CALCULATED PROPERTIES

• Acid pKa: 18.108286
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.107512765
• LogD (pH = 7.4): 0.107512765
• Log P: 0.107512765
• Molar Refractivity: 25.4879 cm^3
• Polarizability: 10.005251 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 165-167°C; 166-166.5 °C(lit.); 56-60°C/13mm
• Flash Point: 131 °F; 55 °C; 62°C(144°F)
• Density: 1.084; 1.084 g/mL at 25 °C(lit.)
• Refractive Index: 1.4530; n20/D 1.452; n20/D 1.452(lit.)
• Hydrophobicity(logP): -0.457

Safety Information

• Storage Warning: Flammable/Keep Cold; IRRITANT
• UN Number: 1224
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10
• TSCA Listed: false; 否
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1224 3/PG 3

Product Information

• Purity: ≥98.5% (GC); 95%; 95+%; 97%; 98%; 99%; min 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H8O2

DETAILS

Sigma Aldrich - 198242

Application
Employed in a study of the enantioselective α-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid.1
Undergoes condensation reactions for the preparation of dipeptides and spiroimidazolones. Employed in Wittig reactions for the synthesis of penicillins and the A ring of Vitamin D3.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 87475

Other Notes
Synthetic intermediate; e.g. for the preparation of the 4-methoxytetrahydropyran-4-yl protecting group1; synthesis of symmetric tetrasubstituted methanes2

REFERENCES

• The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran, L02731, that no new asymmetric center is introduced on reaction with a chiral alcohol: J. Am. Chem. Soc., 89, 3366 (1967); Tetrahedron, 26, 1023, 1031 (1970).